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A chiral (alkoxy)methyl-substituted silicon group as an auxiliary for the stereoselective cuprate addition to $\alpha,\beta$-unsaturated ketones: synthesis of (−)-(R)-phenyl 2-phenylpropyl ketone


Bratovanov, Svestoslav; Bienz, Stefan (1997). A chiral (alkoxy)methyl-substituted silicon group as an auxiliary for the stereoselective cuprate addition to $\alpha,\beta$-unsaturated ketones: synthesis of (−)-(R)-phenyl 2-phenylpropyl ketone. Tetrahedron: Asymmetry, 8(10):1587-1603.

Abstract

The [(benzyloxy)methyl](tert-butyl)methylsilyl group was used as the chiral auxiliary to effect highly diastereoselective conjugate additions of organocuprates to enones. Thus, reaction of several R2CuLi with ct-silylated cx,13-unsaturated ketones afforded the respective addition products with rr-face selectivities of up to 99%. Starting with an optically active substrate, enantiomerically enriched (-)-(R)-phenyl 2-phenylpropyl ketone was prepared with virtually no loss of chiral information in a reaction sequence involving cuprate addition, hydrolysis, and removal of the silicon group.

Abstract

The [(benzyloxy)methyl](tert-butyl)methylsilyl group was used as the chiral auxiliary to effect highly diastereoselective conjugate additions of organocuprates to enones. Thus, reaction of several R2CuLi with ct-silylated cx,13-unsaturated ketones afforded the respective addition products with rr-face selectivities of up to 99%. Starting with an optically active substrate, enantiomerically enriched (-)-(R)-phenyl 2-phenylpropyl ketone was prepared with virtually no loss of chiral information in a reaction sequence involving cuprate addition, hydrolysis, and removal of the silicon group.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1997
Deposited On:25 Aug 2017 13:30
Last Modified:20 Feb 2018 08:38
Publisher:Elsevier
ISSN:0957-4166
OA Status:Closed
Publisher DOI:https://doi.org/10.1016/S0957-4166(97)00134-1

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