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Anti ‐Selective and Diastereofacially Selective Aldol Reactions with ( R )‐2‐Siloxy‐1,2,2‐triphenylethyl propionate
Author(s) -
Braun Manfred,
Sacha Huber
Publication year - 1991
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199113181
Subject(s) - propionate , enantiomer , chemistry , adduct , aldol reaction , aldehyde , zirconium , medicinal chemistry , organic chemistry , catalysis
The zirconium enolate of the ( R )‐propionate 1 attacks aldehydes preferentially at the Si side to afford anti ‐configurated adducts. The chiral auxiliary triphenylglycol, which is the precursor to the ester 1 , is easily accessible in both enantiomeric forms. Thus, access to the carboxylic acids 2 and diols 3 is provided with enantiomeric excesses of > 94%.