Header

UZH-Logo

Maintenance Infos

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.

Statistics

Citations

Dimensions.ai Metrics
28 citations in Web of Science®
27 citations in Scopus®
19 citations in Microsoft Academic
Google Scholar™

Altmetrics

Downloads

0 downloads since deposited on 24 Aug 2017
0 downloads since 12 months

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:20 Feb 2018 12:47
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
OA Status:Closed
Publisher DOI:https://doi.org/10.1002/hlca.19930760507

Download