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

John R. Scheffer; Keyan Wang

doi:10.1055/s-2001-15056

PAPER

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;

Abstract

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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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References

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