Tandem benzannulation cyclization strategy for the synthesis of highly-substituted indoles

ORGN 940

Tin Yiu Lam, tammy@mit.edu and Rick L. Danheiser. Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139
Vinylketenes (generated in situ from cyclobutenones or α-diazo ketones) react with ynamides via a pericyclic cascade process to produce highly-substituted aniline derivatives. Cyclization of the benzannulation products can then be achieved via several alternate procedures leading to indoles that are highly substituted on the benzenoid ring. This talk will focus on the scope, limitations, and mechanism of this new tandem strategy.

 

Heterocycles and Aromatics
8:00 AM-12:00 PM, Thursday, August 23, 2007 BCEC -- 254 A/B, Oral

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007