A Dash of Proline Makes Things Sweet

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Science  17 Sep 2004:
Vol. 305, Issue 5691, pp. 1725-1726
DOI: 10.1126/science.1103026

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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.