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Chiral acylsilanes in organic synthesis. Part 2. The role of the solvent, the organometallic reagent, and the nature of the substrate for the diastereoselectivity of 1,2-additions to racemic alkoxymethyl-substituted acylsilanes


Chapeaurouge, Alexander; Bienz, Stefan (1993). Chiral acylsilanes in organic synthesis. Part 2. The role of the solvent, the organometallic reagent, and the nature of the substrate for the diastereoselectivity of 1,2-additions to racemic alkoxymethyl-substituted acylsilanes. Helvetica Chimica Acta, 76(5):1876-1889.

Abstract

The role of the solvent, the organometallic reagent, and the nature of the substrate for the diastereoselectivity of 1,2-additions to racemic alkoxymethyl-substituted acylsilanes was investigated with the acylsilanes 1a–d by variation of the reaction parameters. The results obtained in this study support strongly the previously proposed preferred ‘chelate-controlled’ reaction path followed under several reaction conditions: highest stereoselectivities were obtained with the best chelating substrates reacting with the most Lewis-acidic organometallic reagents in the least donating solvents. It is shown that almost complete stereoselectivity can be obtained using optimal reaction conditions.

Abstract

The role of the solvent, the organometallic reagent, and the nature of the substrate for the diastereoselectivity of 1,2-additions to racemic alkoxymethyl-substituted acylsilanes was investigated with the acylsilanes 1a–d by variation of the reaction parameters. The results obtained in this study support strongly the previously proposed preferred ‘chelate-controlled’ reaction path followed under several reaction conditions: highest stereoselectivities were obtained with the best chelating substrates reacting with the most Lewis-acidic organometallic reagents in the least donating solvents. It is shown that almost complete stereoselectivity can be obtained using optimal reaction conditions.

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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:11 August 1993
Deposited On:24 Aug 2017 18:26
Last Modified:24 Aug 2017 18:26
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
Publisher DOI:https://doi.org/10.1002/hlca.19930760507

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