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Asymmetric reduction of β‐ketoesters and chiral β‐iminoesters: Impact of a α‐quaternary stereocenter
Author(s) -
Almahli Hadia,
Hendra Frédéric,
Troufflard Claire,
Cavé Christian,
Joseph Delphine,
DelarueCochin Sandrine
Publication year - 2011
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20909
Subject(s) - stereocenter , diastereomer , chemistry , chirality (physics) , stereoselectivity , reduction (mathematics) , stereochemistry , enantioselective synthesis , organic chemistry , catalysis , chiral symmetry , nambu–jona lasinio model , physics , geometry , mathematics , quantum mechanics , quark
Diastereomeric reduction of nonactivated, hindered β‐keto and chiral β‐iminoesters are described. The influence of a α‐stereocontrolled center on the efficiency and stereoselectivity of the reduction was studied. Reaction conditions were optimized to synthesize β‐hydroxy‐ and β‐aminoesters in good yields. In the case of chiral β‐iminoesters, influence of matched/mismatched diastereomeric pairs has been assessed. Chirality, 2011. © 2010 Wiley‐Liss, Inc.