The importance of A-strain in the stereochemical control of ring opening of tetrahydropyrans
The importance of A-strain in the stereochemical control of ring opening of tetrahydropyrans
Readily available cyclic beta-alkoxy-alpha,beta-unsaturated trifluoromethylketones react with excess phenyl magnesium bromide by initial 1,4-addition, followed by ring opening to give a variety of products. Both the major products, unsaturated diols, and the minor products, as shown by X-ray diffraction studies, are generated with high stereoselectivity, which is attributed to A(1,3)-strain.
allylic strain, grignard reagents, tetrahydropyrans
diastereoselective synthesis, allylic 1, 3-strain, epoxidation
7387-7390
Mellor, J. M.
d9b993ad-31be-4f91-8ea3-1723cd1c23bc
El-Sagheer, A. H.
c37c0aa8-20a2-4fd9-b2cf-3a891182db00
16 September 2000
Mellor, J. M.
d9b993ad-31be-4f91-8ea3-1723cd1c23bc
El-Sagheer, A. H.
c37c0aa8-20a2-4fd9-b2cf-3a891182db00
Mellor, J. M. and El-Sagheer, A. H.
(2000)
The importance of A-strain in the stereochemical control of ring opening of tetrahydropyrans.
Tetrahedron Letters, 41 (38), .
(doi:10.1016/S0040-4039(00)01256-9).
Abstract
Readily available cyclic beta-alkoxy-alpha,beta-unsaturated trifluoromethylketones react with excess phenyl magnesium bromide by initial 1,4-addition, followed by ring opening to give a variety of products. Both the major products, unsaturated diols, and the minor products, as shown by X-ray diffraction studies, are generated with high stereoselectivity, which is attributed to A(1,3)-strain.
This record has no associated files available for download.
More information
Published date: 16 September 2000
Keywords:
allylic strain, grignard reagents, tetrahydropyrans
diastereoselective synthesis, allylic 1, 3-strain, epoxidation
Identifiers
Local EPrints ID: 19005
URI: http://eprints.soton.ac.uk/id/eprint/19005
ISSN: 0040-4039
PURE UUID: 310047ef-be7e-41dc-9ec3-8641d945aedc
Catalogue record
Date deposited: 15 Dec 2005
Last modified: 15 Mar 2024 06:10
Export record
Altmetrics
Contributors
Author:
J. M. Mellor
Author:
A. H. El-Sagheer
Download statistics
Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.
View more statistics