A Highly Reactive and Enantioselective Bifunctional Organocatalyst for the Methanolytic Desymmetrization of Cyclic Anhydrides: Prevention of Catalyst Aggregation

Abstract

Unprecedented reactivity and high stereoselectivity were observed in the ring opening of meso anhydrides under mild conditions with a cinchona-alkaloid-based sulfonamide catalyst (see scheme). Computation of the catalyst–transition-state analogue (right; gray C, white H, green F, blue N, red O, yellow S) provided insight into the origin of the stereoselectivity. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2008/z801636_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.