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Efficient route to highly functionalized tetrahydrofurans by stereocontrolled silicon-directed cyclization

✍ Scribed by F. L. van Delft; G. A. van der Marel; J. H. van Boom

Book ID: 104589643
Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 179 KB
Volume: 113
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19941130608

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✦ Synopsis

Abstract

Cyclization of 3,4,6‐tri‐O‐benzyl‐2,5‐di‐O‐trimethylsilyl‐1‐deoxy‐1‐phenyldiisopropylsilyl‐L‐glucitol in the presence of BF~3~·Et~2~O or catalytic H~2~SO~4~ proceeds stereoselectively to give predominantly the fully benzylated 2,5‐anhydro‐L‐glucitol derivative without occurrence of the Peterson elimination.

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