Meerwein–Ponndorf–Verley reaction of α-ketoepoxides. A stereocontrolled one-step synthesis of epoxy-1,3-diol monoesters
Identifieur interne : 000966 ( Istex/Corpus ); précédent : 000965; suivant : 000967Meerwein–Ponndorf–Verley reaction of α-ketoepoxides. A stereocontrolled one-step synthesis of epoxy-1,3-diol monoesters
Auteurs : Apiwat Baramee ; Narongsak Chaichit ; Poolsak Intawee ; Chachanat Thebtaranonth ; Yodhathai ThebtaranonthSource :
- Journal of the Chemical Society, Chemical Communications [ 0022-4936 ] ; 1991.
English descriptors
- KwdEn :
- Teeft :
Abstract
Lithium enolate 3, derived from ketoepoxide 1, adds to two molecules of an aldehyde with concomitant hydride transfer to produce 5 stereospecifically.
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DOI: 10.1039/C39910001016
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A stereocontrolled one-step synthesis of epoxy-1,3-diol monoesters</title><genre><json:string>article</json:string></genre><host><title>Journal of the Chemical Society, Chemical Communications</title><language><json:string>unknown</json:string></language><issn><json:string>0022-4936</json:string></issn><issue>15</issue><pages><first>1016</first><last>1017</last><total>2</total></pages><genre><json:string>journal</json:string></genre></host><categories><inist><json:string>sciences appliquees, technologies et medecines</json:string><json:string>sciences biologiques et medicales</json:string><json:string>sciences biologiques fondamentales et appliquees. psychologie</json:string></inist></categories><publicationDate>1991</publicationDate><copyrightDate>1991</copyrightDate><doi><json:string>10.1039/C39910001016</json:string></doi><id>AC9226BDAECF238382321A9152285014C8289919</id><score>1</score><fulltext><json:item><extension>pdf</extension><original>true</original><mimetype>application/pdf</mimetype><uri>https://api.istex.fr/document/AC9226BDAECF238382321A9152285014C8289919/fulltext/pdf</uri></json:item><json:item><extension>zip</extension><original>false</original><mimetype>application/zip</mimetype><uri>https://api.istex.fr/document/AC9226BDAECF238382321A9152285014C8289919/fulltext/zip</uri></json:item><istex:fulltextTEI uri="https://api.istex.fr/document/AC9226BDAECF238382321A9152285014C8289919/fulltext/tei"><teiHeader><fileDesc><titleStmt><title level="a">Meerwein–Ponndorf–Verley reaction of α-ketoepoxides. 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A stereocontrolled one-step synthesis of epoxy-1,3-diol monoesters</title><author xml:id="author-0000"><persName><forename type="first">Apiwat</forename><surname>Baramee</surname></persName></author><author xml:id="author-0001"><persName><forename type="first">Narongsak</forename><surname>Chaichit</surname></persName></author><author xml:id="author-0002"><persName><forename type="first">Poolsak</forename><surname>Intawee</surname></persName></author><author xml:id="author-0003"><persName><forename type="first">Chachanat</forename><surname>Thebtaranonth</surname></persName></author><author xml:id="author-0004"><persName><forename type="first">Yodhathai</forename><surname>Thebtaranonth</surname></persName></author><idno type="istex">AC9226BDAECF238382321A9152285014C8289919</idno><idno type="ark">ark:/67375/QHD-W67NBF4W-9</idno><idno type="DOI">10.1039/C39910001016</idno><idno type="ms-id">C39910001016</idno></analytic><monogr><title level="j">Journal of the Chemical Society, Chemical Communications</title><title level="j" type="abbrev">J. Chem. Soc., Chem. Commun.</title><idno type="pISSN">0022-4936</idno><idno type="eISSN"></idno><imprint><publisher>RSC</publisher><date type="published" when="1991"></date><biblScope unit="issue">15</biblScope><biblScope unit="page" from="1016">1016</biblScope><biblScope unit="page" to="1017">1017</biblScope></imprint></monogr></biblStruct></sourceDesc></fileDesc><profileDesc><creation><date>1991</date></creation><langUsage><language ident="en">en</language></langUsage><abstract><p>Lithium enolate 3, derived from ketoepoxide 1, adds to two molecules of an aldehyde with concomitant hydride transfer to produce 5 stereospecifically.</p></abstract></profileDesc><revisionDesc><change when="1991">Published</change></revisionDesc></teiHeader></istex:fulltextTEI><json:item><extension>txt</extension><original>false</original><mimetype>text/plain</mimetype><uri>https://api.istex.fr/document/AC9226BDAECF238382321A9152285014C8289919/fulltext/txt</uri></json:item></fulltext><metadata><istex:metadataXml wicri:clean="corpus rsc-journals not found" wicri:toSee="no header"><istex:xmlDeclaration>version="1.0" encoding="UTF-8"</istex:xmlDeclaration><istex:document><article xsi:schemaLocation="http://www.rsc.org/schema/rscart38 http://www.rsc.org/schema/rscart38/rscart38.xsd" dtd="RSCART3.8" type="ART"><art-admin><ms-id>C39910001016</ms-id><doi>10.1039/C39910001016</doi></art-admin><published type="print"><journalref><link>C3</link></journalref><volumeref><link></link></volumeref><issueref><link>15</link></issueref><pubfront><fpage>1016</fpage><lpage>1017</lpage><no-of-pages>2</no-of-pages><date><year>1991</year></date></pubfront></published><published type="subsyear"><journalref><link>C3</link></journalref><pubfront><fpage></fpage><lpage></lpage><no-of-pages></no-of-pages><date><year>1991</year></date></pubfront></published><art-front><titlegrp><title>Meerwein–Ponndorf–Verley reaction of α-ketoepoxides. A stereocontrolled one-step synthesis of epoxy-1,3-diol monoesters</title></titlegrp><authgrp><author><person><persname><fname>Apiwat</fname><surname>Baramee</surname></persname></person></author><author><person><persname><fname>Narongsak</fname><surname>Chaichit</surname></persname></person></author><author><person><persname><fname>Poolsak</fname><surname>Intawee</surname></persname></person></author><author><person><persname><fname>Chachanat</fname><surname>Thebtaranonth</surname></persname></person></author><author><person><persname><fname>Yodhathai</fname><surname>Thebtaranonth</surname></persname></person></author></authgrp><abstract><p>Lithium enolate <bo>3</bo>, derived from ketoepoxide <bo>1</bo>, adds to two molecules of an aldehyde with concomitant hydride transfer to produce <bo>5</bo> stereospecifically.</p></abstract></art-front><art-body><section type="PDFExtract"><title></title><p> J. CHEM. SOC. CHEM. COMMUN. 1991 Meerwein-Ponndorf-Verley Reaction of a-Ketoepoxides. A Stereocontrolled One-step Synthesis of Epoxy-I,3-diol Monoesters Apiwat Baramee,a Narongsak Chaichit,b Poolsak Intawee b Chachanat Thebtaranontha and Yodhathai Thebtaranonth" a a Department of Chemistry Faculty of Science Mahidol University Rama 6 Bangkok 10400 Thailand b Department of Physics Faculty of Science Silpakorn University Nakorn Pathom 73000 Thailand Lithium enolate 3 derived from ketoepoxide 1 adds to two molecules of an aldehyde with concomitant hydride transfer to produce 5 stereospecifically. It has been known for some time1 that certain enolizable a-halo and a-methoxy ketones upon treatment with lithium diisopropylamide (LDA) undergo reduction in a Meerwein- Ponndorf-Verley fashion2 in addition to the expected enolatc formation. </p><p>This type of reaction has lately gained interest amongst chemists and is finding useful applications in organic synthesis. A recent example which prompted us to record our findings is that by Evans3 where a samarium-catalysed reaction between a P-hydroxy ketone and an aldehyde leads via a cyclic transition state to a 1,3-diol. Here we report that the carbonyl group a- to an epoxide function (e.g. 1) is exceptionally prone to the Meerwein-Ponndorf-Verley hydride transfer reaction. Thus treatment of racemic 1with one equivalent of LDA at various temperatures invariably produces after protonation alcohol 2 as a single stereoisomer in 18-23% isolated yields,? together with recovered starting material 1 (50-62%) appar- ently from protonation of enolate 3. </p><p>However by simple modification i. e. substituting lithium tetramethylpiperidide (LTMP a lithium amide base with no a-hydrogen) for LDA we find that 3 can be specifically generated and employed as a ,Ph ,Ph 0 OH OH 0 1 2 3 4 This is an example of a stereospecific Meerwein-Ponndorf-Verle y reduction of acyclic ketone by LDA [cf. Ref. 11. The relative stereochemistry of 2 has not been determined. nucleophile. Accordingly reaction of 1 with LTMP in tetrahydrofuran (THF) at -78 "C followed by quenching with an alkyl halide affords the corresponding alkylated product in good yield (7446%). Trapping enolate 3 with one equivalent of benzaldehyde at -78°C in THF in the absence of a chelating agent followed by immediate work-up yields 4 (58%) as a mixture of two stereoisomers together with recovered 1 (30%). </p><p>At higher temperatures and longer reaction times (i. e. room temperature overnight) however 4 is detected (TLC) only as a minor component in the crude reaction product which is composed mainly of a single isomer of 5a (26%) and recovered 1(59%). 7 Ph 0 II0 5 a; R = Ph 8 b; R = 4-OMe-C6H4 c; R = 4-Me-C6H4 J. CHEM. SOC. CHEM. COMMUN. 1991 been noted that addition of the first molecule of benzaldehyde to 3 is non-stereospecific giving 4 as a mixture of stereoisom-ers. The mechanistic picture of the reaction did not improve until a surprising observation was made in that treatment of 4 3 R$!p Ph 0 OLi 0 6 t 0 II PhCO OH H R+q$ 111 ptl*ph OH 0 4 5a Scheme 2 d Fig. </p><p>1 ORTEP drawing of compound 5a We have been able to promote the formation of 5a by increasing the ratio of aldehyde. Thus treatment of enolate 3 with excess of benzaldehyde (3 equiv.) followed by stirring overnight at room temperature results in a single isomer of compound 5a (63%) again accompanied by starting material 1 (27%). This behaviour appears to be quite general and reproducible for example single isomers of 5b-f are obtained when the corresponding aldehydes are employed. $ Mechanistically the above reaction might at first be en- visaged as involving consecutive additions of enolate 3 to two molecules of aldehyde followed by a Meerwein-Ponndorf- Verley hydride transfer as illustrated in Scheme 1. </p><p>However Scheme 1 suffers a serious drawback in failing to justify the specific stereochemistry of final product 5 it having already $ 5b 56% (36); Sc 60% (26); 5d 74% (18); 5e 71% (19); Sf,46% (40) purified yields as calculated from 1 (number in parentheses indicates percentage of recovered starting material 1). All compounds described are fully characterized. Elemental analyses were performed by the Scientific and Technological Research Equipment Centre Chulalongkorn University Bangkok and by the Elemental Analysis Unit Department of Chemistry Faculty of Science Silpakorn University Nakorn Pathom. D Accompanied by 1 and recovered 4 in yields of 15 and 10% respectively. </p><p> (isomeric mixture) with equimolar amounts of base (BunLi LDA or LTMP) and benzaldehyde also yields a single isomer of 5a (47%) identical in all respects with that obtained earlier.0 The fact that the same stereoisomer of 5a is obtained whether from 3 or an isomeric mixture of 4 seems to us to suggest that the addition of 3 (generated either from 1or from a retroaldol reaction of 4) to the two molecules of aldehyde as well as the hydride transfer all occur in a concerted fashion involving a cyclic transition state 9 in which all large substituents occupy equatorial positions.7 In fact cyclic transition states have been proposed earlier by MolandeI-4 and Evans3 for the samarium-catalysed Reformatsky and Meer- wein-Ponndorf-Verley reactions. </p><p>Here it is interesting to note the exclusive approach of the first molecule of benzal- dehyde on the apparently less hindered side of starting epoxy-enolate 3. Transition state model 9 nicely accommo- dates our experimental results in that stereospecific produc- tion of 5 is possible either from 1or an isomeric mixture of 4. It is also probable that an equilibrium exists between 3 and 9 under the conditions employed judging from the fact that we were unable to drive the reaction to completion (Scheme 2).$ The stereochemical integrity of 5a is fully confirmed by X-ray analysis (Fig. 1).11Also the use of deuteriated benzal- dehyde in the reaction with 3 gives as anticipated the corresponding deuteriated 5a.** This reaction provides an expedient and stereocontrolled entry to epoxy 1,3-diol monoesters such as 5 by simultaneous creation of both diol chiral centres in one single operation. </p><p> Received 6th March 1991; Cum. 1101075A References 1 C. Kowalski X. Creary A. J. Rollin and M. C. Burke J. Org. Chem. 1978,43 2601. 2 A. L. Wilds Org. Reactions 1944 2 178. 3 D. A. Evans and A. H. Hoveyda J. Am. Chem. SOC.,1990 112 6447. 4 G. A. Molander and J. B. Etter J. Am. Chem. Soc. 1987 109 6556. 7 It is arguable that the step-wise mechanism in Scheme 1is still viable since the isolation of isomeric aldol products 4 was carried out under kinetically controlled conditions (-78 "C) whereas at higher temper- atures a retroaldol-aldol process might first allow interconversion to a single thermodynamically more stable isomer of 4 which would then proceed to the single final product 5. </p><p> 11 Crystal data for 5a C&H2604 monoclinic s ace group n1/cwith a = 17.312(8) b = 6.090(2) c = 21.675(8) 1,p = 96.53(3)" V = 2270(2) A3and D = 1.177 g ~rn-~ for Z = 4. The structure was solved by direct methods using the XTAL 88 program system which revealed the positions of all of the non-hydrogen atoms; R = 0.062. Atomic coordinates bond lengths and angles and thermal parameters have been deposited at the Cambridge Crystailographic Data Centre. See notice to Authors Issue No. 1. ** Deuteriated benzaldehyde (~0.5 atom d) was prepared by H +D exchange of the corresponding aminonitrile precursor (cf. S. F. Dyke E. P. Tiley A. W. C. White and D. P. Gale Tetrahedron 1975,31 1219). Determination of deuterium incorporation was made by NMR analysis. </p></section></art-body><art-back><biblist><citgroup id="cit1"><journalcit><citauth><fname>C.</fname><surname>Kowalski</surname></citauth><citauth><fname>X.</fname><surname>Creary</surname></citauth><citauth><fname>A. J.</fname><surname>Rollin</surname></citauth><citauth><fname>M. C.</fname><surname>Burke</surname></citauth><title>J. Org. Chem.</title><year>1978</year><volumeno>43</volumeno><pages><fpage>2601</fpage></pages></journalcit></citgroup><citgroup id="cit2"><journalcit><citauth><fname>A. L.</fname><surname>Wilds</surname></citauth><title>Org. Reactions</title><year>1944</year><volumeno>2</volumeno><pages><fpage>178</fpage></pages></journalcit></citgroup><citgroup id="cit3"><journalcit><citauth><fname>D. A.</fname><surname>Evans</surname></citauth><citauth><fname>A. H.</fname><surname>Hoveyda</surname></citauth><title>J. Am. Chem. Soc.</title><year>1990</year><volumeno>112</volumeno><pages><fpage>6447</fpage></pages></journalcit></citgroup><citgroup id="cit4"><journalcit><citauth><fname>G. A.</fname><surname>Molander</surname></citauth><citauth><fname>J. B.</fname><surname>Etter</surname></citauth><title>J. Am. Chem. Soc.</title><year>1987</year><volumeno>109</volumeno><pages><fpage>6556</fpage></pages></journalcit></citgroup></biblist><compoundgrp></compoundgrp><annotationgrp></annotationgrp><datagrp></datagrp><resourcegrp></resourcegrp></art-back></article></istex:document></istex:metadataXml><mods version="3.6"><titleInfo><title>Meerwein–Ponndorf–Verley reaction of α-ketoepoxides. 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