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Chiral Borane–Amine Adducts in Asymmetric Synthesis: Alkylation of Alanine Derivatives
Author(s) -
Ferey Vincent,
Toupet Loïc,
Le Gall Thierry,
Mioskowski Charles
Publication year - 1996
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.199604301
Subject(s) - diastereomer , alkylation , chemistry , borane , enantiomer , adduct , amine gas treating , nitrogen atom , enantioselective synthesis , medicinal chemistry , stereochemistry , organic chemistry , catalysis , ring (chemistry)
Enantiomeric excesses of up to 82% are obtained for the α,α‐disubstituted products 4 arising from alkylation reactions of borane–amine adducts 2 and 3 , which have a chiral nitrogen atom. The structure of diastereomer 2 , which can be obtained selectively in the boration of 1 , has been established by single‐crystal X‐ray analysis.