ORGN 559 |
| Previous studies in our laboratory have shown that the carbamate and N-acyl derivatives of aminosulfones undergo intramolecular cyclization upon treatment with base to give lactams and dihydropyrrolidines. We have now shown that other electron withdrawing groups such as sulfoxides and phosphonates can facilitate an analogous carbamate cyclization. When treated with LHMDS in THF, the carbamate derivatives I undergo intramolecular cyclization to yield the corresponding lactams II in excellent yields. The N-acyl phosphonate III cyclizes to yield the dihydropyrrolidine IV in good yields. However, the corresponding sulfoxide did not yield the desired product under these conditions. Some preliminary studies of the reactivities of the cyclization products including applications for stereoselective synthesis of functionalized pyrrolidine derivatives will be reported.
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New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster
Sci-Mix
Division of Organic Chemistry |
