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Synthesis 2001(8): 1253-1257
DOI: 10.1055/s-2001-15056
PAPER
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Photochemical Synthesis of a β-Lactam via the Solid State Ionic Chiral Auxiliary Method

John R. Scheffer*, Keyan Wang
Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, Canada V6T 1Z1
Fax: +1(604)8222847; e-Mail: scheffer@chem.ubc.ca;
Further Information

Publication History

Received 29 January 2001
Publication Date:
24 September 2004 (online)

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Abstract

Photolysis of crystals of a carboxylic acid-containing N,N-dialkylarylglyoxylamide to which an optically pure ammonium ion (the ionic chiral auxiliary) has been attached through a salt bridge leads to a 91 % isolated yield of a β-lactam in greater than 99 % enantiomeric excess. Suspension of the crystals in hexane allows the photoreaction to be carried out on a 500 mg scale, thus demonstrating the synthetic utility of the solid state ionic chiral auxiliary approach to asymmetric synthesis.

Key words

β-lactam - asymmetric synthesis - chiral auxiliaries - photochemistry - solid state

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