Mellor, J. M. and El-Sagheer, A. H.
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).
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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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