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Dimerization of Lithiated Terminal Aziridines
Author(s) -
Hodgson David M.,
Miles Steven M.
Publication year - 2006
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.200503303
Subject(s) - enantiopure drug , terminal (telecommunication) , olefin fiber , computer science , combinatorial chemistry , chemistry , scheme (mathematics) , core (optical fiber) , stereochemistry , enantioselective synthesis , catalysis , organic chemistry , mathematics , computer network , mathematical analysis , telecommunications
Let's get together : Dimerization of enantiopure terminal aziridines by lithiation gives efficiently N‐protected 2‐ene‐1,4‐diamines with complete selectivity for the E olefin (see scheme). The usefulness of the method was demonstrated in a concise synthesis of ( R , S , S , R )‐2,5‐diamino‐1,6‐diphenylhexane‐3,4‐diol, the core unit of many extremely potent HIV protease inhibitors and also asymmetric catalysts.