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Chiral silicon groups as auxiliaries for enantioselective synthesis: access to optically active silanes by biotransformation and the enantiospecific preparation of (R)-(+)-1-phenylethanol


Huber, Priska; Bratovanov, Svetoslav; Bienz, Stefan; Syldatk, Christoph; Pietzsch, Markus (1996). Chiral silicon groups as auxiliaries for enantioselective synthesis: access to optically active silanes by biotransformation and the enantiospecific preparation of (R)-(+)-1-phenylethanol. Tetrahedron: Asymmetry, 7(1):69-78.

Abstract

The synthesis of the optically active alkoxymethyl-substituted acetylsilanes (+)-3 and (−)-b was achieved by the bioreduction of (±)-3 with resting cells of Trigonopsis variabilis to the diastereoisomeric alcohols (+)-4 and (+)-5. These two compounds were separated by chromatography and separately reoxidized to the desired optically active silyl ketones. As a simple example of the use of chiral alkoxymethyl-substituted silyl groups as auxiliaries for the synthesis of enantiomerically enriched silicon-free compounds, the chelate controlled 1,2-addition of phenyl lithium to (−)-3 and the stereospecific conversion of the corresponding major addition product to (R)-(+)-1-phenylethanol (+)-10 is presented.
Silane (±)-3 was reduced by Trigonopsis variabilis (DSM 70714) to (+)-4 and (+)-5, which were separated and oxidized to (R)-(−)-3 and (S)-(+)-3. (R)-(−)-3 was finally converted to (R-(+)-1-phenylethanol [(R)-(+)-12].

Abstract

The synthesis of the optically active alkoxymethyl-substituted acetylsilanes (+)-3 and (−)-b was achieved by the bioreduction of (±)-3 with resting cells of Trigonopsis variabilis to the diastereoisomeric alcohols (+)-4 and (+)-5. These two compounds were separated by chromatography and separately reoxidized to the desired optically active silyl ketones. As a simple example of the use of chiral alkoxymethyl-substituted silyl groups as auxiliaries for the synthesis of enantiomerically enriched silicon-free compounds, the chelate controlled 1,2-addition of phenyl lithium to (−)-3 and the stereospecific conversion of the corresponding major addition product to (R)-(+)-1-phenylethanol (+)-10 is presented.
Silane (±)-3 was reduced by Trigonopsis variabilis (DSM 70714) to (+)-4 and (+)-5, which were separated and oxidized to (R)-(−)-3 and (S)-(+)-3. (R)-(−)-3 was finally converted to (R-(+)-1-phenylethanol [(R)-(+)-12].

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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:1996
Deposited On:24 Aug 2017 16:44
Last Modified:24 Aug 2017 16:44
Publisher:Elsevier
ISSN:0957-4166
Publisher DOI:https://doi.org/10.1016/0957-4166(95)00422-X

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