TiCl4 Mediated LiBH4 reduction of β-ketophosphine oxides: a high stereoselective route to the synthesis of anti - β -hydroxyphosphine oxides
Identifieur interne : 000428 ( Istex/Corpus ); précédent : 000427; suivant : 000429TiCl4 Mediated LiBH4 reduction of β-ketophosphine oxides: a high stereoselective route to the synthesis of anti - β -hydroxyphosphine oxides
Auteurs : Giuseppe Bartoli ; Marcella Bosco ; Letizia Sambri ; Enrico MarcantoniSource :
- Tetrahedron Letters [ 0040-4039 ] ; 1996.
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Abstract
Abstract: The reduction of an α-alkyl-β-ketophosphine oxide with LiBH4 in presence of a strong chelating agent, such as TiCl4, gives the corresponding β-hydroxyphosphine oxide in high yields and with high anti-diastereoselectivity independently from the size of both the α- and β-alkyl chains.
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DOI: 10.1016/0040-4039(96)01601-2
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Sambri</name><affiliation><mods:affiliation>Dipartimento di Chimica Organica “A.Mangini”, v.le Risorgimento, 4, I-40136, Bologna, Italy</mods:affiliation></affiliation></author><author><name sortKey="Marcantoni, Enrico" sort="Marcantoni, Enrico" uniqKey="Marcantoni E" first="Enrico" last="Marcantoni">Enrico Marcantoni</name><affiliation><mods:affiliation>Dipartimento di Scienze Chimiche, via S.Agostino 1, I-62032 Camerino (MC, Italy</mods:affiliation></affiliation></author></analytic><monogr></monogr><series><title level="j">Tetrahedron Letters</title><title level="j" type="abbrev">TETL</title><idno type="ISSN">0040-4039</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="1996">1996</date><biblScope unit="volume">37</biblScope><biblScope unit="issue">41</biblScope><biblScope unit="page" from="7421">7421</biblScope><biblScope unit="page" to="7424">7424</biblScope></imprint><idno type="ISSN">0040-4039</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0040-4039</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Alkyl</term><term>Alkyl substituents</term><term>Chem</term><term>Ester</term><term>High selectivity</term><term>High yields</term><term>Ketophosphine oxides</term><term>Libh4</term><term>Lithium</term><term>Methodology</term><term>Oxide</term><term>Ph2p</term><term>Ph2po</term><term>Phch</term><term>Room temperature</term><term>Selectivity</term><term>Stereospecific decomposition</term><term>Strong chelating agent</term><term>Tici4</term><term>Typical procedure</term></keywords><keywords scheme="Teeft" xml:lang="en"><term>Alkyl</term><term>Alkyl substituents</term><term>Chem</term><term>Ester</term><term>High selectivity</term><term>High yields</term><term>Ketophosphine oxides</term><term>Libh4</term><term>Lithium</term><term>Methodology</term><term>Oxide</term><term>Ph2p</term><term>Ph2po</term><term>Phch</term><term>Room temperature</term><term>Selectivity</term><term>Stereospecific decomposition</term><term>Strong chelating agent</term><term>Tici4</term><term>Typical procedure</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Abstract: The reduction of an α-alkyl-β-ketophosphine oxide with LiBH4 in presence of a strong chelating agent, such as TiCl4, gives the corresponding β-hydroxyphosphine oxide in high yields and with high anti-diastereoselectivity independently from the size of both the α- and β-alkyl chains.</div></front></TEI><istex><corpusName>elsevier</corpusName><keywords><teeft><json:string>chem</json:string><json:string>alkyl</json:string><json:string>ester</json:string><json:string>tici4</json:string><json:string>libh4</json:string><json:string>ph2p</json:string><json:string>lithium</json:string><json:string>phch</json:string><json:string>ph2po</json:string><json:string>high 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type="first">Letizia</forename><surname>Sambri</surname></persName><affiliation>Dipartimento di Chimica Organica “A.Mangini”, v.le Risorgimento, 4, I-40136, Bologna, Italy</affiliation></author><author xml:id="author-0003"><persName><forename type="first">Enrico</forename><surname>Marcantoni</surname></persName><affiliation>Dipartimento di Scienze Chimiche, via S.Agostino 1, I-62032 Camerino (MC, Italy</affiliation></author><idno type="istex">3FABE6D8B46D7D32C0D75012C3B738992036A587</idno><idno type="DOI">10.1016/0040-4039(96)01601-2</idno><idno type="PII">0040-4039(96)01601-2</idno></analytic><monogr><title level="j">Tetrahedron Letters</title><title level="j" type="abbrev">TETL</title><idno type="pISSN">0040-4039</idno><idno type="PII">S0040-4039(00)X0059-7</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="1996"></date><biblScope unit="volume">37</biblScope><biblScope unit="issue">41</biblScope><biblScope unit="page" from="7421">7421</biblScope><biblScope 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oxides: a high stereoselective route to the synthesis of <ce:italic>anti</ce:italic>-<ce:italic>β</ce:italic>-hydroxyphosphine oxides</ce:title><ce:author-group><ce:author><ce:given-name>Giuseppe</ce:given-name><ce:surname>Bartoli</ce:surname><ce:ranking><ce:sup>∗</ce:sup></ce:ranking></ce:author><ce:author><ce:given-name>Marcella</ce:given-name><ce:surname>Bosco</ce:surname></ce:author><ce:author><ce:given-name>Letizia</ce:given-name><ce:surname>Sambri</ce:surname></ce:author><ce:affiliation><ce:textfn>Dipartimento di Chimica Organica “A.Mangini”, v.le Risorgimento, 4, I-40136, Bologna, Italy</ce:textfn></ce:affiliation></ce:author-group><ce:author-group><ce:author><ce:given-name>Enrico</ce:given-name><ce:surname>Marcantoni</ce:surname></ce:author><ce:affiliation><ce:textfn>Dipartimento di Scienze Chimiche, via S.Agostino 1, I-62032 Camerino (MC, Italy</ce:textfn></ce:affiliation></ce:author-group><ce:date-received day="5" month="7" year="1996"></ce:date-received><ce:date-revised day="9" month="8" year="1996"></ce:date-revised><ce:date-accepted day="15" month="8" year="1996"></ce:date-accepted><ce:abstract><ce:section-title>Abstract</ce:section-title><ce:abstract-sec><ce:simple-para>The reduction of an α-alkyl-β-ketophosphine oxide with LiBH<ce:inf>4</ce:inf> in presence of a strong chelating agent, such as TiCl<ce:inf>4</ce:inf>, gives the corresponding β-hydroxyphosphine oxide in high yields and with high <ce:italic>anti</ce:italic>-diastereoselectivity independently from the size of both the α- and β-alkyl chains.</ce:simple-para></ce:abstract-sec></ce:abstract><ce:abstract class="graphical"><ce:abstract-sec><ce:simple-para>Reduction of α-alkyl-β-ketophosphine oxides with TiCl<ce:inf>4</ce:inf>LiBH<ce:inf>4</ce:inf> give α-alkyl-β-hydroxyphosphine oxides in high yields.</ce:simple-para></ce:abstract-sec><ce:figure><ce:link locator="gr1"></ce:link></ce:figure></ce:abstract></head></converted-article></istex:document></istex:metadataXml><mods version="3.6"><titleInfo><title>TiCl4 Mediated LiBH4 reduction of β-ketophosphine oxides: a high stereoselective route to the synthesis of anti - β -hydroxyphosphine oxides</title></titleInfo><titleInfo type="alternative" contentType="CDATA"><title>TiCl</title></titleInfo><name type="personal"><namePart type="given">Giuseppe</namePart><namePart type="family">Bartoli</namePart><affiliation>Dipartimento di Chimica Organica “A.Mangini”, v.le Risorgimento, 4, I-40136, Bologna, Italy</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Marcella</namePart><namePart type="family">Bosco</namePart><affiliation>Dipartimento di Chimica Organica “A.Mangini”, v.le Risorgimento, 4, I-40136, Bologna, Italy</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Letizia</namePart><namePart type="family">Sambri</namePart><affiliation>Dipartimento di Chimica Organica “A.Mangini”, v.le Risorgimento, 4, I-40136, Bologna, Italy</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Enrico</namePart><namePart type="family">Marcantoni</namePart><affiliation>Dipartimento di Scienze Chimiche, via S.Agostino 1, I-62032 Camerino (MC, Italy</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="research-article" displayLabel="Full-length article" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-1JC4F85T-7">research-article</genre><originInfo><publisher>ELSEVIER</publisher><dateIssued encoding="w3cdtf">1996</dateIssued><dateModified encoding="w3cdtf">1996-08-09</dateModified><copyrightDate encoding="w3cdtf">1996</copyrightDate></originInfo><language><languageTerm type="code" authority="iso639-2b">eng</languageTerm><languageTerm type="code" 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