| 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 |
| Journal | Synthesis-Stuttgart |
| Pagination | 1253-1257 |
| Type of Article | Article |
| ISBN Number | 0039-7881 |
| Keywords | ACHIRAL 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 |
