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The importance of A-strain in the stereochemical control of ring opening of tetrahydropyrans

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), pp. 7387-7390. (doi:10.1016/S0040-4039(00)01256-9).

Record type: Article


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.

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Published date: 16 September 2000
Keywords: allylic strain, grignard reagents, tetrahydropyrans diastereoselective synthesis, allylic 1, 3-strain, epoxidation


Local EPrints ID: 19005
ISSN: 0040-4039
PURE UUID: 310047ef-be7e-41dc-9ec3-8641d945aedc

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Date deposited: 15 Dec 2005
Last modified: 17 Jul 2017 16:34

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Author: J. M. Mellor
Author: A. H. El-Sagheer

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