Oxa-Michael and Baylis-Hillman strategies toward synthesis of sultam libraries

ORGN 73

Christopher A. Knudtson, snocrash@ku.edu1, Aihua Zhou1, Hetal Shah1, Paul VanderVelde, paul.vandervelde@hope.edu2, and Paul R. Hanson, phanson@ku.edu1. (1) Department of Chemistry, University of Kansas, 1251 Wescoe Hall Dr, NIH Center of Excellence in Chemical Methodologies and Library Development (KU-CMLD), Lawrence, KS 66045-7582, (2) Department of Chemistry, Hope College, 35 E. 12th Street, Holland, MI 49422
The development of Baylis-Hillman and oxa-Michael methodologies for the synthesis of sultam (cyclic sulfonamides) from chiral non-racemic amino alcohols is reported. These methods make use of a central vinyl sulfonamide lynchpin to afford a variety of diverse sultam scaffolds. A library of 4,4-dioxo-1,4,5-oxathiazepines has been synthesized in a one-pot protocol utilizing a TBAF-initiated domino deprotection/ oxa-Michael cyclization methodology. In addition, the synthesis of a library of Baylis-Hillman derived 1,1-dioxo-5-methylene-isothiazolidin-4-ols and subsequent diversification in a one-pot procedure utilizing ROMP-derived polymeric reagents and scavangers is detailed.

 

Physical Organic Chemistry, Combinatorial and Process Chemistry, New Reactions and Methodology, Peptides, Proteins and Amino Acids
8:00 PM-10:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008