P-chirogenic organocatalysts: application to the aza-Morita-Baylis-Hillman (aza-MBH) reaction of ketimines

Shinobu Takizawa; Emmanuelle Remond; Fernando Arteaga Arteaga; Yasushi Yoshida; Vellaisamy Sridharan; Jerome Bayardon; Sylvain Juge; Hiroaki Sasai

doi:10.1039/c3cc44549f

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P-chirogenic organocatalysts: application to the aza-Morita-Baylis-Hillman (aza-MBH) reaction of ketimines

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P-chirogenic organocatalysts: application to the aza-Morita-Baylis-Hillman (aza-MBH) reaction of ketimines

Shinobu Takizawa, Emmanuelle Remond, Fernando Arteaga Arteaga, Yasushi Yoshida, Vellaisamy Sridharan, Jerome Bayardon, Sylvain Juge et Hiroaki Sasai

Chemical communications (Cambridge, England), Vol.49(75), pp.8392-8394

01/01/2013

DOI: https://doi.org/10.1039/c3cc44549f

PMID: 23939137

Résumé

Chemistry

Chemistry, Multidisciplinary

Physical Sciences

Science & Technology

The P-chirogenic organocatalysts were found to promote the enantioselective aza-Morita-Baylis-Hillman reaction of ketimines derived from acyclic alpha-keto esters. In the P-chirogenic organocatalyzed aza-MBH reactions, alpha,alpha-disubstituted alpha-amino acid derivatives were obtained in high yields with high enantioselectivities (up to 97% ee).

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Titre: P-chirogenic organocatalysts: application to the aza-Morita-Baylis-Hillman (aza-MBH) reaction of ketimines
Créateurs - sans rôle: Shinobu Takizawa - Osaka Univ, Inst Sci & Ind Res, Ibaraki, Osaka 5670047, Japan
Emmanuelle Remond - Univ Bourgogne, ICMUB StereochIM, F-21078 Dijon, France
Fernando Arteaga Arteaga - Osaka Univ, Inst Sci & Ind Res, Ibaraki, Osaka 5670047, Japan
Yasushi Yoshida - Osaka Univ, Inst Sci & Ind Res, Ibaraki, Osaka 5670047, Japan
Vellaisamy Sridharan - Osaka Univ, Inst Sci & Ind Res, Ibaraki, Osaka 5670047, Japan
Jerome Bayardon - Univ Bourgogne, ICMUB StereochIM, F-21078 Dijon, France
Sylvain Juge - Univ Bourgogne, ICMUB StereochIM, F-21078 Dijon, France
Hiroaki Sasai - Osaka Univ, Inst Sci & Ind Res, Ibaraki, Osaka 5670047, Japan
Détails de publication: Chemical communications (Cambridge, England), Vol.49(75), pp.8392-8394
Éditeur: Royal Soc Chemistry
Nombre de pages: 3
Note de subvention: CNRS (Centre National de la Recherche Scientifique); Centre National de la Recherche Scientifique (CNRS) Japan Science and Technology Corporation; Japan Science & Technology Agency (JST) Agence Nationale de la Recherche; Agence Nationale de la Recherche (ANR) 24590009; 24105518; 13J07348; 24106726 / Grants-in-Aid for Scientific Research; Ministry of Education, Culture, Sports, Science and Technology, Japan (MEXT); Japan Society for the Promotion of Science; Grants-in-Aid for Scientific Research (KAKENHI) Ministere de l'Education National et de la Recherche Ministry of Education, Culture, Sports, Science and Technology, Japan; Ministry of Education, Culture, Sports, Science and Technology, Japan (MEXT)
Identifiants: 99139014509311
Unité académique: Institut des Biomolécules Max Mousseron - IBMM
Langue: English
Type de ressource: Journal article