Synthesis 2014; 46(07): 871-878
DOI: 10.1055/s-0033-1340818
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

The Practical Preparation of Chiral N-Sulfonyl Oxaziridines via Catalytic Asymmetric Payne Oxidation

Ryosuke Tsutsumi
a  Institute of Transformative Bio-Molecules (WPI-ITbM) and Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho B2-3(611), Chikusa, Nagoya 464-8603, Japan
,
Seonwoo Kim
a  Institute of Transformative Bio-Molecules (WPI-ITbM) and Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho B2-3(611), Chikusa, Nagoya 464-8603, Japan
,
Daisuke Uraguchi
a  Institute of Transformative Bio-Molecules (WPI-ITbM) and Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho B2-3(611), Chikusa, Nagoya 464-8603, Japan
,
Takashi Ooi*
a  Institute of Transformative Bio-Molecules (WPI-ITbM) and Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho B2-3(611), Chikusa, Nagoya 464-8603, Japan
b  CREST, Japan Science and Technology Agency (JST), Chikusa, Nagoya 464-8603, Japan   Fax: +81(52)7893338   Email: tooi@apchem.nagoya-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 27 November 2013

Accepted after revision: 22 January 2014

Publication Date:
21 February 2014 (eFirst)

Abstract

The asymmetric Payne oxidation of N-sulfonyl imines catalyzed by a P-spiro chiral triaminoiminophosphorane was developed for the practical synthesis of optically active N-sulfonyl oxaziridines. High efficiency and an excellent level of enantioselectivity were generally achieved with a wide variety of aldimines by choosing appropriate reaction conditions. The versatility of this method was demonstrated by the diastereoselective kinetic oxidation of racemic α-chiral N-sulfonyl imines.

 
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