Indium-Mediated Addition of γ-Substituted Allylic Halides to N-Aryl α-Imino Esters: Diastereoselective Production of β,β'-Disubstituted α-Amino Acid Derivatives with Two Contiguous Stereocenters
Identifieur interne : 001982 ( Main/Repository ); précédent : 001981; suivant : 001983Indium-Mediated Addition of γ-Substituted Allylic Halides to N-Aryl α-Imino Esters: Diastereoselective Production of β,β'-Disubstituted α-Amino Acid Derivatives with Two Contiguous Stereocenters
Auteurs : RBID : Pascal:12-0441849Descripteurs français
- Pascal (Inist)
- Indium, Composé allylique, Halogène composé organique, Composé aromatique, Iminoester, Diastéréosélectivité, Aminoacide, Chélation, Imine, Ester, Fonctionnalisation, Composé insaturé, Allylation, Cyclisation, Métathèse, Synthèse chimique, Stéréochimie, Diffraction RX, Structure moléculaire, Réaction de Barbier.
English descriptors
- KwdEn :
- Allylation, Allylic compound, Aminoacid, Aromatic compound, Barbier reaction, Chelation, Chemical synthesis, Cyclization, Diastereoselectivity, Ester, Functionalization, Imine, Iminoester, Indium, Metathesis, Molecular structure, Organic halogen compounds, Stereochemistry, Unsaturated compound, X ray diffraction.
Abstract
Chelation-controlled Barbier-type indium-mediated addition of γ-substituted allylic halides to N-aryl (including N-PMP) α-imino- and N-acylhydrazono esters and highly diastereoselective tailoring of functionalized γ,δ-unsaturated β,β'-disubstituted N-aryl α-amino acid derivatives, bearing two contiguous stereocenters is reported. Further N-allylation of the resulting γ,δ-unsaturated β,β'-disubstituted N-aryl amino acid derivatives followed by ring closing metathesis (RCM) led to the synthesis of 2,3-disubstituted N-aryltetrahydropyridine derivatives bearing two contiguous stereocenters. The stereochemistry of the key products was unequivocally established from X-ray structure analyses.
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en" level="a">Indium-Mediated Addition of γ-Substituted Allylic Halides to N-Aryl α-Imino Esters: Diastereoselective Production of β,β'-Disubstituted α-Amino Acid Derivatives with Two Contiguous Stereocenters</title><author><name>NAYYAR AHMAD ASLAM</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER) Mohali, Knowledge City, Sector 81, SAS Nagar, Mohali, Manauli P. O</s1><s2>Punjab, 140306</s2><s3>IND</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>6 aut.</sZ></inist:fA14><country>Inde</country><wicri:noRegion>Punjab, 140306</wicri:noRegion></affiliation></author><author><name sortKey="Rajkumar, Vadla" uniqKey="Rajkumar V">Vadla Rajkumar</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER) Mohali, Knowledge City, Sector 81, SAS Nagar, Mohali, Manauli P. O</s1><s2>Punjab, 140306</s2><s3>IND</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>6 aut.</sZ></inist:fA14><country>Inde</country><wicri:noRegion>Punjab, 140306</wicri:noRegion></affiliation></author><author><name sortKey="Reddy, Chennakesava" uniqKey="Reddy C">Chennakesava Reddy</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER) Mohali, Knowledge City, Sector 81, SAS Nagar, Mohali, Manauli P. O</s1><s2>Punjab, 140306</s2><s3>IND</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>6 aut.</sZ></inist:fA14><country>Inde</country><wicri:noRegion>Punjab, 140306</wicri:noRegion></affiliation></author><author><name sortKey="Yasuda, Makoto" uniqKey="Yasuda M">Makoto Yasuda</name><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka</s1><s2>Suita, Osaka 565-0871</s2><s3>JPN</s3><sZ>4 aut.</sZ><sZ>5 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Suita, Osaka 565-0871</wicri:noRegion></affiliation></author><author><name sortKey="Baba, Akio" uniqKey="Baba A">Akio Baba</name><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka</s1><s2>Suita, Osaka 565-0871</s2><s3>JPN</s3><sZ>4 aut.</sZ><sZ>5 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Suita, Osaka 565-0871</wicri:noRegion></affiliation></author><author><name>SRINIVASARAO ARULANANDA BABU</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER) Mohali, Knowledge City, Sector 81, SAS Nagar, Mohali, Manauli P. O</s1><s2>Punjab, 140306</s2><s3>IND</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>6 aut.</sZ></inist:fA14><country>Inde</country><wicri:noRegion>Punjab, 140306</wicri:noRegion></affiliation></author></titleStmt><publicationStmt><idno type="inist">12-0441849</idno><date when="2012">2012</date><idno type="stanalyst">PASCAL 12-0441849 INIST</idno><idno type="RBID">Pascal:12-0441849</idno><idno type="wicri:Area/Main/Corpus">001572</idno><idno type="wicri:Area/Main/Repository">001982</idno></publicationStmt><seriesStmt><idno type="ISSN">1434-193X</idno><title level="j" type="abbreviated">Eur. j. org. chem. : (Print)</title><title level="j" type="main">European journal of organic chemistry : (Print)</title></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Allylation</term><term>Allylic compound</term><term>Aminoacid</term><term>Aromatic compound</term><term>Barbier reaction</term><term>Chelation</term><term>Chemical synthesis</term><term>Cyclization</term><term>Diastereoselectivity</term><term>Ester</term><term>Functionalization</term><term>Imine</term><term>Iminoester</term><term>Indium</term><term>Metathesis</term><term>Molecular structure</term><term>Organic halogen compounds</term><term>Stereochemistry</term><term>Unsaturated compound</term><term>X ray diffraction</term></keywords><keywords scheme="Pascal" xml:lang="fr"><term>Indium</term><term>Composé allylique</term><term>Halogène composé organique</term><term>Composé aromatique</term><term>Iminoester</term><term>Diastéréosélectivité</term><term>Aminoacide</term><term>Chélation</term><term>Imine</term><term>Ester</term><term>Fonctionnalisation</term><term>Composé insaturé</term><term>Allylation</term><term>Cyclisation</term><term>Métathèse</term><term>Synthèse chimique</term><term>Stéréochimie</term><term>Diffraction RX</term><term>Structure moléculaire</term><term>Réaction de Barbier</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Chelation-controlled Barbier-type indium-mediated addition of γ-substituted allylic halides to N-aryl (including N-PMP) α-imino- and N-acylhydrazono esters and highly diastereoselective tailoring of functionalized γ,δ-unsaturated β,β'-disubstituted N-aryl α-amino acid derivatives, bearing two contiguous stereocenters is reported. Further N-allylation of the resulting γ,δ-unsaturated β,β'-disubstituted N-aryl amino acid derivatives followed by ring closing metathesis (RCM) led to the synthesis of 2,3-disubstituted N-aryltetrahydropyridine derivatives bearing two contiguous stereocenters. The stereochemistry of the key products was unequivocally established from X-ray structure analyses.</div></front></TEI><inist><standard h6="B"><pA><fA01 i1="01" i2="1"><s0>1434-193X</s0></fA01><fA03 i2="1"><s0>Eur. j. org. chem. : (Print)</s0></fA03><fA06><s2>23</s2></fA06><fA08 i1="01" i2="1" l="ENG"><s1>Indium-Mediated Addition of γ-Substituted Allylic Halides to N-Aryl α-Imino Esters: Diastereoselective Production of β,β'-Disubstituted α-Amino Acid Derivatives with Two Contiguous Stereocenters</s1></fA08><fA11 i1="01" i2="1"><s1>NAYYAR AHMAD ASLAM</s1></fA11><fA11 i1="02" i2="1"><s1>RAJKUMAR (Vadla)</s1></fA11><fA11 i1="03" i2="1"><s1>REDDY (Chennakesava)</s1></fA11><fA11 i1="04" i2="1"><s1>YASUDA (Makoto)</s1></fA11><fA11 i1="05" i2="1"><s1>BABA (Akio)</s1></fA11><fA11 i1="06" i2="1"><s1>SRINIVASARAO ARULANANDA BABU</s1></fA11><fA14 i1="01"><s1>Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER) Mohali, Knowledge City, Sector 81, SAS Nagar, Mohali, Manauli P. O</s1><s2>Punjab, 140306</s2><s3>IND</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>6 aut.</sZ></fA14><fA14 i1="02"><s1>Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka</s1><s2>Suita, Osaka 565-0871</s2><s3>JPN</s3><sZ>4 aut.</sZ><sZ>5 aut.</sZ></fA14><fA20><s1>4395-4411</s1></fA20><fA21><s1>2012</s1></fA21><fA23 i1="01"><s0>ENG</s0></fA23><fA43 i1="01"><s1>INIST</s1><s2>26693</s2><s5>354000508143350160</s5></fA43><fA44><s0>0000</s0><s1>© 2012 INIST-CNRS. All rights reserved.</s1></fA44><fA45><s0>26 ref.</s0></fA45><fA47 i1="01" i2="1"><s0>12-0441849</s0></fA47><fA60><s1>P</s1></fA60><fA61><s0>A</s0></fA61><fA64 i1="01" i2="1"><s0>European journal of organic chemistry : (Print)</s0></fA64><fA66 i1="01"><s0>DEU</s0></fA66><fC01 i1="01" l="ENG"><s0>Chelation-controlled Barbier-type indium-mediated addition of γ-substituted allylic halides to N-aryl (including N-PMP) α-imino- and N-acylhydrazono esters and highly diastereoselective tailoring of functionalized γ,δ-unsaturated β,β'-disubstituted N-aryl α-amino acid derivatives, bearing two contiguous stereocenters is reported. Further N-allylation of the resulting γ,δ-unsaturated β,β'-disubstituted N-aryl amino acid derivatives followed by ring closing metathesis (RCM) led to the synthesis of 2,3-disubstituted N-aryltetrahydropyridine derivatives bearing two contiguous stereocenters. The stereochemistry of the key products was unequivocally established from X-ray structure analyses.</s0></fC01><fC02 i1="01" i2="X"><s0>001C02B04</s0></fC02><fC03 i1="01" i2="X" l="FRE"><s0>Indium</s0><s2>NC</s2><s5>01</s5></fC03><fC03 i1="01" i2="X" l="ENG"><s0>Indium</s0><s2>NC</s2><s5>01</s5></fC03><fC03 i1="01" i2="X" l="SPA"><s0>Indio</s0><s2>NC</s2><s5>01</s5></fC03><fC03 i1="02" i2="X" l="FRE"><s0>Composé allylique</s0><s5>02</s5></fC03><fC03 i1="02" i2="X" l="ENG"><s0>Allylic compound</s0><s5>02</s5></fC03><fC03 i1="02" i2="X" l="SPA"><s0>Compuesto alílico</s0><s5>02</s5></fC03><fC03 i1="03" i2="3" l="FRE"><s0>Halogène composé organique</s0><s5>03</s5></fC03><fC03 i1="03" i2="3" l="ENG"><s0>Organic halogen compounds</s0><s5>03</s5></fC03><fC03 i1="04" i2="X" l="FRE"><s0>Composé aromatique</s0><s5>04</s5></fC03><fC03 i1="04" i2="X" l="ENG"><s0>Aromatic compound</s0><s5>04</s5></fC03><fC03 i1="04" i2="X" l="SPA"><s0>Compuesto aromático</s0><s5>04</s5></fC03><fC03 i1="05" i2="X" l="FRE"><s0>Iminoester</s0><s5>05</s5></fC03><fC03 i1="05" i2="X" l="ENG"><s0>Iminoester</s0><s5>05</s5></fC03><fC03 i1="05" i2="X" l="SPA"><s0>Iminoester</s0><s5>05</s5></fC03><fC03 i1="06" i2="X" l="FRE"><s0>Diastéréosélectivité</s0><s5>06</s5></fC03><fC03 i1="06" i2="X" l="ENG"><s0>Diastereoselectivity</s0><s5>06</s5></fC03><fC03 i1="06" i2="X" l="SPA"><s0>Diastereoselectividad</s0><s5>06</s5></fC03><fC03 i1="07" i2="X" l="FRE"><s0>Aminoacide</s0><s5>07</s5></fC03><fC03 i1="07" i2="X" l="ENG"><s0>Aminoacid</s0><s5>07</s5></fC03><fC03 i1="07" i2="X" l="SPA"><s0>Aminoácido</s0><s5>07</s5></fC03><fC03 i1="08" i2="X" l="FRE"><s0>Chélation</s0><s5>08</s5></fC03><fC03 i1="08" i2="X" l="ENG"><s0>Chelation</s0><s5>08</s5></fC03><fC03 i1="08" i2="X" l="SPA"><s0>Quelación</s0><s5>08</s5></fC03><fC03 i1="09" i2="X" l="FRE"><s0>Imine</s0><s5>09</s5></fC03><fC03 i1="09" i2="X" l="ENG"><s0>Imine</s0><s5>09</s5></fC03><fC03 i1="09" i2="X" l="SPA"><s0>Imina</s0><s5>09</s5></fC03><fC03 i1="10" i2="X" l="FRE"><s0>Ester</s0><s5>10</s5></fC03><fC03 i1="10" i2="X" l="ENG"><s0>Ester</s0><s5>10</s5></fC03><fC03 i1="10" i2="X" l="SPA"><s0>Ester</s0><s5>10</s5></fC03><fC03 i1="11" i2="X" l="FRE"><s0>Fonctionnalisation</s0><s5>11</s5></fC03><fC03 i1="11" i2="X" l="ENG"><s0>Functionalization</s0><s5>11</s5></fC03><fC03 i1="11" i2="X" l="SPA"><s0>Funciónalización</s0><s5>11</s5></fC03><fC03 i1="12" i2="X" l="FRE"><s0>Composé insaturé</s0><s5>12</s5></fC03><fC03 i1="12" i2="X" l="ENG"><s0>Unsaturated compound</s0><s5>12</s5></fC03><fC03 i1="12" i2="X" l="SPA"><s0>Compuesto insaturado</s0><s5>12</s5></fC03><fC03 i1="13" i2="X" l="FRE"><s0>Allylation</s0><s5>13</s5></fC03><fC03 i1="13" i2="X" l="ENG"><s0>Allylation</s0><s5>13</s5></fC03><fC03 i1="13" i2="X" l="SPA"><s0>Alilación</s0><s5>13</s5></fC03><fC03 i1="14" i2="X" l="FRE"><s0>Cyclisation</s0><s5>14</s5></fC03><fC03 i1="14" i2="X" l="ENG"><s0>Cyclization</s0><s5>14</s5></fC03><fC03 i1="14" i2="X" l="SPA"><s0>Ciclización</s0><s5>14</s5></fC03><fC03 i1="15" i2="X" l="FRE"><s0>Métathèse</s0><s5>15</s5></fC03><fC03 i1="15" i2="X" l="ENG"><s0>Metathesis</s0><s5>15</s5></fC03><fC03 i1="15" i2="X" l="SPA"><s0>Metatesis</s0><s5>15</s5></fC03><fC03 i1="16" i2="X" l="FRE"><s0>Synthèse chimique</s0><s5>16</s5></fC03><fC03 i1="16" i2="X" l="ENG"><s0>Chemical synthesis</s0><s5>16</s5></fC03><fC03 i1="16" i2="X" l="SPA"><s0>Síntesis química</s0><s5>16</s5></fC03><fC03 i1="17" i2="X" l="FRE"><s0>Stéréochimie</s0><s5>17</s5></fC03><fC03 i1="17" i2="X" l="ENG"><s0>Stereochemistry</s0><s5>17</s5></fC03><fC03 i1="17" i2="X" l="SPA"><s0>Estereoquímica</s0><s5>17</s5></fC03><fC03 i1="18" i2="X" l="FRE"><s0>Diffraction RX</s0><s5>18</s5></fC03><fC03 i1="18" i2="X" l="ENG"><s0>X ray diffraction</s0><s5>18</s5></fC03><fC03 i1="18" i2="X" l="SPA"><s0>Difracción RX</s0><s5>18</s5></fC03><fC03 i1="19" i2="X" l="FRE"><s0>Structure moléculaire</s0><s5>19</s5></fC03><fC03 i1="19" i2="X" l="ENG"><s0>Molecular structure</s0><s5>19</s5></fC03><fC03 i1="19" i2="X" l="SPA"><s0>Estructura molecular</s0><s5>19</s5></fC03><fC03 i1="20" i2="X" l="FRE"><s0>Réaction de Barbier</s0><s4>CD</s4><s5>96</s5></fC03><fC03 i1="20" i2="X" l="ENG"><s0>Barbier reaction</s0><s4>CD</s4><s5>96</s5></fC03><fN21><s1>345</s1></fN21><fN44 i1="01"><s1>OTO</s1></fN44><fN82><s1>OTO</s1></fN82></pA></standard></inist></record>Pour manipuler ce document sous Unix (Dilib)
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