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Enantioselective Synthesis and Stereoselective Ring Opening of N ‐Acylaziridines
Author(s) -
Cockrell Jennifer,
Wilhelmsen Christopher,
Rubin Heather,
Martin Allen,
Morgan Jeremy B.
Publication year - 2012
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.201204224
Subject(s) - enantioselective synthesis , aziridine , enantiomer , ring (chemistry) , stereoselectivity , nucleophile , kinetic resolution , chemistry , combinatorial chemistry , stereochemistry , computer science , catalysis , organic chemistry
Kinetic resolution of N ‐acylaziridines by nucleophilic ring opening was achieved with ( R )‐BINOL as the chiral modifier under boron‐catalyzed conditions (see scheme; Ar=3,5‐dinitrophenyl). The consumed enantiomer of aziridine can be further converted to an enantioenriched 1,2‐chloroamide with recovery of ( R )‐BINOL.