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Enantioselective Synthesis of β‐Amino Acids: TMS‐SAMP as a Chiral Ammonia Equivalent for the Aza Analogous Michael Addition to α,β‐Unsaturated Esters
Author(s) -
Enders Dieter,
Wahl Heiner,
Bettray Wolfgang
Publication year - 1995
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.199504551
Subject(s) - enantioselective synthesis , stereoselectivity , enantiomer , michael reaction , chemistry , stereochemistry , alkyl , amino acid , ammonia , organic chemistry , catalysis , biochemistry
The N‐silylated chiral amines TMS‐SAMP and TMS‐RAMP can be employed for stereoselective CN bond formation with enantiomeric excesses of 90‐80%. In these reactions, the corresponding hydrazinoesters are formed initially, which are subsequently cleaved hydrogenolytically to give the desired β‐amino acids 1 . R = alkyl, R′ = Me, t Bu.