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Synthesis of chiral allenes by peterson-type olefinations


Bratovanov, Svetoslav; Bienz, Stefan (1996). Synthesis of chiral allenes by peterson-type olefinations. Main Group Metal Chemistry, 19(12):769.

Abstract

Chiral 1,3-disubstituted allenes have been prepared by means of a Peterson-type elimination in yields as high as 95%. To obtain optically active allenes, the [(benzyloxy)methyl](fert-butyl)methylsilyl group was used as the chiral auxiliary to get an optically enriched elimination precursor. Unfortunately, the elimination reaction with this compound to the respective allene was not stereospecific. Only racemic allene was obtained, probably due to a reaction course via a carbocationic intermediate (Ei rather than E2 mechanism).

Abstract

Chiral 1,3-disubstituted allenes have been prepared by means of a Peterson-type elimination in yields as high as 95%. To obtain optically active allenes, the [(benzyloxy)methyl](fert-butyl)methylsilyl group was used as the chiral auxiliary to get an optically enriched elimination precursor. Unfortunately, the elimination reaction with this compound to the respective allene was not stereospecific. Only racemic allene was obtained, probably due to a reaction course via a carbocationic intermediate (Ei rather than E2 mechanism).

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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:31 Oct 2017 15:44
Last Modified:20 Feb 2018 08:51
Publisher:Walter de Gruyter GmbH
ISSN:0792-1241
OA Status:Green
Publisher DOI:https://doi.org/10.1515/MGMC.1996.19.12.769

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