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Enantioselective photochemical synthesis of a beta-lactam via the solid state ionic chiral auxiliary method

TitleEnantioselective photochemical synthesis of a beta-lactam via the solid state ionic chiral auxiliary method
Publication TypeJournal Article
Year of Publication2001
AuthorsScheffer, JR, Wang, KY
JournalSynthesis-Stuttgart
Pagination1253-1257
Type of ArticleArticle
ISBN Number0039-7881
KeywordsACHIRAL OXO AMIDE, ACID, asymmetric synthesis, beta-lactam, chiral auxiliaries, CRYSTALLINE STATE, HOST, INCLUSION COMPLEXES, PHOTOCHEMISTRY, PHOTOCYCLIZATION, solid state
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 beta -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 stare ionic chiral auxiliary approach to asymmetric synthesis.

URL<Go to ISI>://000169617900022