Stereoselective cyclopropanation of enamides

ORGN 423

Ting Lu, tlu4@wisc.edu, Zhenlei Song, zsong2@wisc.edu, Richard P. Hsung, rphsung@pharmacy.wisc.edu, Ziyad F. Al-Rashid, Changhong Ko, cko3@wisc.edu, and Yu Tang, ytang4@wisc.edu. Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin-Madison, 777 Highland Ave., Rennebohm Hall, Madison, WI 53705
Simmons-Smith reaction and its variations are the most useful methods for diastereoselective formation of cyclopropane moieties. Herein, we study the diastereoselective synthesis of cyclopropyl amides from the chiral auxiliary derived enamides under the modified Simmons-Smith reaction conditions. A variety of chiral cyclopropyl amides were obtained in up to 80% yield and with up to >95:5 dr. Electronic effects and steric effects on the reactivity and diastereoselectivity of this reaction were also investigated.

 

New Reactions and Methodology, Total Synthesis, Materials, Devices and Switches, Lipids, Nucleotides and Mimetics
8:00 PM-10:00 PM, Tuesday, March 27, 2007 Hyatt Regency Chicago -- Riverside Center, Poster

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007