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Diastereoselectivity during 2-pyridone photo-[4+4] cycloaddition. The tribenzylsilyl protecting group

✍ Scribed by Scott McN Sieburth; Christina B Madsen-Duggan; Fangning Zhang

Book ID: 104231014
Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 176 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)00953-4

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✦ Synopsis

The use of a silyloxy group as a stereocontrol element on the most distant carbon of a pyrindinone during intermolecular [4+4] photocycloaddition was tested using silyl groups varying in size (tert-butyldimethylsilyl<triisopropylsilyl< tribenzylsilyl). The ratio of the diastereomeric products was proportional to the size of the silyl group, with the largest, tribenzylsilyl, giving the best ratio of 10:1. The expected stereochemistry was confirmed by X-ray crystallography.

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