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

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

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 o...

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Veröffentlicht in:Synthesis (Stuttgart) 2001-01, Vol.112 (8)
Hauptverfasser: Scheffer, John R., Wang, Keyan
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Wang, Keyan
description 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.
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title Enantioselective Photochemical Synthesis of a β-Lactam via the Solid State Ionic Chiral Auxiliary Method
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