Header

UZH-Logo

Maintenance Infos

More than a protective group: synthesis and applications of a new chiral silane


Campagna, Maurizio; Trzoss, Michael; Bienz, Stefan (2007). More than a protective group: synthesis and applications of a new chiral silane. Organic Letters, 9(19):3793-3796.

Abstract

Enantiomerically pure (-)-(R)- and (+)-(S)-(1-methoxy-2,2,2-triphenylethyl)dimethylsilanes (MOTES-H) were synthesized from triphenylacetaldehyde in five synthetic steps and with 60% overall yield. MOTES-protected alpha- and beta-hydroxycarbonyl compounds were used in Grignard and Diels-Alder reactions in the presence of MgBr2 to afford addition products with 87-98% yield and selectivities of up to >120:1 dr. With this method, the pine beetle pheromone (-)-frontalin (67%, 98.5% ee) and naturally occurring (-)-(R)-octane-1,3-diol (90%, >99% ee) were synthesized.

Abstract

Enantiomerically pure (-)-(R)- and (+)-(S)-(1-methoxy-2,2,2-triphenylethyl)dimethylsilanes (MOTES-H) were synthesized from triphenylacetaldehyde in five synthetic steps and with 60% overall yield. MOTES-protected alpha- and beta-hydroxycarbonyl compounds were used in Grignard and Diels-Alder reactions in the presence of MgBr2 to afford addition products with 87-98% yield and selectivities of up to >120:1 dr. With this method, the pine beetle pheromone (-)-frontalin (67%, 98.5% ee) and naturally occurring (-)-(R)-octane-1,3-diol (90%, >99% ee) were synthesized.

Statistics

Citations

7 citations in Web of Science®
8 citations in Scopus®
Google Scholar™

Altmetrics

Downloads

0 downloads since deposited on 23 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:22 August 2007
Deposited On:23 Aug 2017 16:43
Last Modified:23 Aug 2017 16:43
Publisher:American Chemical Society (ACS)
ISSN:1523-7052
Publisher DOI:https://doi.org/10.1021/ol071382h
PubMed ID:17713916

Download

Preview Icon on Download
Content: Published Version
Language: English
Filetype: PDF - Registered users only
Size: 245kB
View at publisher