The Mitsunobu Reaction of Tetrachlorophthalimide

Zhaozhong J. Jia; Sandra Kelberlau; Lars Olsson; G. Anilkumar; Bert Fraser-Reid

doi:10.1055/s-1999-2680

Synlett 1999; 1999(5): 565-566
DOI: 10.1055/s-1999-2680

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The Mitsunobu Reaction of Tetrachlorophthalimide

Zhaozhong J. Jia^* , Sandra Kelberlau, Lars Olsson, G. Anilkumar, Bert Fraser-Reid

^*Natural Products and Glycotechnology Research Institute, Inc., 4118 Swarthmore Road, Durham, NC 27707, USA; Fax 91 94 93 61 13; E-mail: dglucose@aol.com

Abstract

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Tetrachlorophthalimide is shown to be an excellent agent for Mitsunobu displacement of primary hydroxyl groups in a wide variety of substrates. Secondary alcohols also react readily, except in carbohydrate derivatives where there is a low rate of success. In a competition experiment between phthalimide and its tetrachloro counterpart, there was no trace of a product from the former.

Mitsunobu - tetrachlorophthalimide - hydroxyl displacement

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