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Science 17 September 2004:
Vol. 305. no. 5691, pp. 1725 - 1726
DOI: 10.1126/science.1103026
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Perspectives

Also see the archival list of Science's Compass: Enhanced Perspectives

CHEMISTRY:
Enhanced: A Dash of Proline Makes Things Sweet

Erik J. Sorensen and Glenn M. Sammis

The special ability of proline to catalyze aldol additions via enamine formation and Brønsted acid activation makes proline a versatile catalyst for enantioselective synthesis. In their Perspective, Sorensen and Sammis discuss the results reported by Northrup and MacMillan, in which proline is used to catalyze the first step of a two-step synthesis of glucose, mannose, and allose. This remarkable stereoselective synthesis uses achiral two-carbon building blocks in the shortest syntheses of these hexoses to date.

The authors are in the Department of Chemistry, Princeton University, Princeton, NJ 08544, USA. E-mail: ejs{at}princeton.edu

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Science. ISSN 0036-8075 (print), 1095-9203 (online)