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Enantio‐ and Diastereoselective Catalytic Mannich‐Type Reaction of a Glycine Schiff Base Using a Chiral Two‐Center Phase‐Transfer Catalyst
Author(s) -
Okada Akihiro,
Shibuguchi Tomoyuki,
Ohshima Takashi,
Masu Hyuma,
Yamaguchi Kentaro,
Shibasaki Masakatsu
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200500927
Subject(s) - schiff base , catalysis , chemistry , glycine , salt (chemistry) , phase (matter) , base (topology) , enantioselective synthesis , tartrate , mannich reaction , organic chemistry , polymer chemistry , combinatorial chemistry , amino acid , mathematical analysis , biochemistry , mathematics
Optically active α,β‐diamino acids are prepared under asymmetric phase‐transfer reaction conditions from a glycine Schiff base and N‐protected imines with a tartrate‐derived diammonium salt (TaDiAS) as the phase‐transfer catalyst (see scheme; Boc= tert ‐butoxycarbonyl). Chemoselective deprotection of the N atoms allows straightforward transformations of the α,β‐diamino acid products to be carried out.