Premium
Highly Diastereoselective Alkylation of Aziridine‐2‐carboxylate Esters: Enantioselective Synthesis of LFA‐1 Antagonist BIRT‐377
Author(s) -
Patwardhan Aniruddha P.,
Pulgam V. Reddy,
Zhang Yu,
Wulff William D.
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.200500923
Subject(s) - aziridine , alkylation , enantioselective synthesis , chemistry , combinatorial chemistry , protecting group , stereochemistry , catalysis , organic chemistry , ring (chemistry) , alkyl
The benzhydryl group is the key : Efficient alkylation of 3‐substituted aziridine‐2‐carboxylates is only possible with N ‐benzhydryl‐protected aziridines and occurs with complete retention of the configuration at the 2‐position. Sequential catalytic asymmetric aziridination and aziridine alkylation reactions have been applied to the synthesis of BIRT‐377 (see structure).