Domino Sakurai/Mukaiyama aldol/Schmidt reactions of azido aldehydes with enones

ORGN 495

Huaxing Pei, jaube@ku.edu, Huey-Lih Lee, D. Srinavasa Reddy, Gagandeep Somal, Yibin Zeng, and Jeffrey Aubé. Department of Medicinal Chemistry, the University of Kansas, 1251 Wescoe Hall Drive, Malott Hall, Room 4070, Lawrence, KS 66045-7582
A new three-stage sequence has been developed to construct bicyclic hydroxy lactams bearing three to five sterogenic centers. In the presence of TiCl4, allyltrimethylsilane underwent 1,4 addition to a series of alpha, beta-unsaturated ketones. This generated a trimethylsilyl enol ether intermediate, which was then reacted with an azido aldehyde or its corresponding acetal. Following Mukaiyama aldol condensation, the reaction continued with an intramolecular Schmidt reaction to afford bicyclic lactam products. The scope and mechanism of this domino process will be discussed.
 

New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006