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Lithiation‐Induced Migrations from Nitrogen to Carbon in Terminal Aziridines
Author(s) -
Hodgson David M.,
Humphreys Philip G.,
Xu Zhaoqing,
Ward John G.
Publication year - 2007
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.200604920
Subject(s) - phosphonate , stereoselectivity , lithium (medication) , chemistry , carbon fibers , terminal (telecommunication) , nitrogen , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , computer science , psychology , catalysis , computer network , composite number , algorithm , psychiatry
Benefiting from deprotection : Lithium 2,2,6,6‐tetramethylpiperidide induces N ‐Boc or N ‐phosphonate terminal aziridines to undergo regio‐ and stereoselective N‐to‐C migration of the protecting group, giving synthetically valuable trans ‐aziridinylesters and trans ‐aziridinylphosphonates.