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Highly Enantioselective Reduction with Novel, Bridged NADH Models
Author(s) -
Kanomata Nobuhiro,
Nakata Tadashi
Publication year - 1997
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.199712071
Subject(s) - phosphorane , enantioselective synthesis , diastereomer , stereochemistry , chemistry , substrate (aquarium) , ring (chemistry) , combinatorial chemistry , organic chemistry , catalysis , biology , ecology
Biomimetic reduction of benzoylformate to mandelate with 97–99% ee was achieved with the diastereomeric, bridge NADH models ( S,S )‐ 1 and ( R,S )‐ 1 . The oligomethylene bridge acts as an “enzyme wall” and hinders the approach of the substrate from one side of the dihydropyridine ring. Isomers 1 were synthesized from the corresponding bridged nicotinate precursor, which was prepared by the reaction of formyl‐substituted (vinylimino)phosphorane with methyl propiolate.