Enantioselective Synthesis of β‐Amino Acids: TMS‐SAMP as a Chiral Ammonia Equivalent for the Aza Analogous Michael Addition to α,β‐Unsaturated Esters | Zendy

Enders Dieter | Zendy; Wahl Heiner | Zendy; Bettray Wolfgang | Zendy

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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.

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