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Highly π‐Facial Stereoselective Aldol Reaction of ( S )‐Proline‐Derived Amide Enolate with Benzaldehydes
Author(s) -
Adam Waldemar,
Zhang Aimin
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200390097
Subject(s) - chemistry , aldol reaction , diastereomer , stereoselectivity , stereocenter , bicyclic molecule , amide , stereochemistry , proline , yield (engineering) , adduct , organic chemistry , enantioselective synthesis , amino acid , catalysis , biochemistry , materials science , metallurgy
The asymmetric aldol reaction of the ( S )‐proline‐derived bicyclic amide enolate 1 with benzaldehydes selectively affords the two diastereomeric aldol adducts (3 S ,3′ R ,8 S )‐ 3a and (3 S ,3′ S ,8 S )‐ 3a , of four possible diastereomers, in good yield. The high control of π‐facial stereoselectivity at the endocyclic C‐3 stereocenter is due to perfect shielding by the pseudo‐axial phenyl ring at the C‐1 position. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)