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Catalyst‐Controlled Multicomponent Aziridination of Chiral Aldehydes
Author(s) -
Mukherjee Munmun,
Zhou Yubai,
Dai Yijing,
Gupta AniL K.,
Pulgam V. Reddy,
Staples Richard J.,
Wulff William D.
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201605955
Subject(s) - enantioselective synthesis , catalysis , chemistry , organic chemistry , ethylene , aldehyde , combinatorial chemistry
A highly diastereoselective and enantioselective method for the multicomponent aziridination of chiral aldehydes has been developed with BOROX catalysts of the VANOL ( 3,3′‐diphenyl‐2,2′‐bi‐1‐naphthol) and VAPOL (2,2′‐diphenyl‐(4‐biphenanthrol)) ligands. Very high to perfect catalyst control is observed with most all substrates examined including aldehydes with chiral centers in the α‐ and β‐positions. High catalyst control was also observed for a number of chiral heterocyclic aldehydes allowing for the preparation of epoxy aziridines, bis(aziridines) and ethylene diaziridines. Application of this reaction in the synthesis of β 3 ‐homo‐ d ‐alloisoleucine and β 3 ‐homo‐ l ‐isoleucine is reported.