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Direct Catalytic Asymmetric Mannich‐Type Reaction of α‐N 3 Amide
Author(s) -
Sun Zhongdong,
Weidner Karin,
Kumagai Naoya,
Shibasaki Masakatsu
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503921
Subject(s) - amide , mannich reaction , catalysis , adduct , chemistry , yield (engineering) , organic chemistry , combinatorial chemistry , enantioselective synthesis , materials science , metallurgy
An α‐N 3 7‐azaindoline amide serves as a latent enolate to directly engage in an asymmetric Mannich‐type reaction with N ‐thiophosphinoyl imines by the action of a cooperative catalyst. The thus‐obtained highly enantioenriched anti ‐adduct was transformed into β‐amino‐α‐azido acid in high yield by simple acidic treatment.