Enantioselective Synthesis and Stereoselective Ring Opening of  N ‐Acylaziridines | Zendy

Cockrell Jennifer | Zendy; Wilhelmsen Christopher | Zendy; Rubin Heather | Zendy; Martin Allen | Zendy; Morgan Jeremy B. | Zendy

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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.

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