|Title||Enantioselective photochemical synthesis of a beta-lactam via the solid state ionic chiral auxiliary method|
|Publication Type||Journal Article|
|Year of Publication||2001|
|Authors||Scheffer, JR, Wang, KY|
|Type of Article||Article|
|Keywords||ACHIRAL OXO AMIDE, ACID, asymmetric synthesis, beta-lactam, chiral auxiliaries, CRYSTALLINE STATE, HOST, INCLUSION COMPLEXES, PHOTOCHEMISTRY, PHOTOCYCLIZATION, solid state|
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|