Control of α/β Stereoselectivity in Lewis Acid Promoted C‐Glycosidations Using a Controlling Anomeric Effect Based on the Conformational Restriction Strategy | Zendy

Tamura Satoru | Zendy; Abe Hiroshi | Zendy; Matsuda Akira | Zendy; Shuto Satoshi | Zendy

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Control of α/β Stereoselectivity in Lewis Acid Promoted C‐Glycosidations Using a Controlling Anomeric Effect Based on the Conformational Restriction Strategy

Author(s) -

Tamura Satoru,

Abe Hiroshi,

Matsuda Akira,

Shuto Satoshi

Publication year - 2003

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200390261

Subject(s) - stereoselectivity , anomer , lewis acids and bases , anomeric effect , chemistry , stereochemistry , organic chemistry , catalysis

The kinetic anomeric effect has been used to control both α and β stereoselectivity in glycosidation reactions. Depending on the restricted conformation 4 C 1 or 1 C 4 of the substrate, the anomeric α ( 1 → 2 ) or β product ( 3 → 4 ) was obtained highly stereoselectively from the Lewis acid promoted anomeric allylation with allyltrimethylsilane (TIPS=triisopropylsilyl).

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