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Copper(I) mediated highly diastereoselective conjugate addition of grignard reagents to 2-silyloxycyclopentenecarboxylates

The conjugate addition of magnesium cuprates to 2-silyloxycyclopentenecarboxylates leads, after desilylation, to 5-substituted-2-hydroxycyclopentanecarboxylates in high yields and diastereoselectivities. The 2-silyloxy derivatives avoid the formation of the SN 2′ reaction by-products. No loss of sel...

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Bibliographic Details
Published in:Tetrahedron letters 1996-08, Vol.37 (35), p.6323-6326
Main Authors: Dambrin, Valéry, Villiéras, Monique, Moreau, Céline, Amri, Hassen, Toupet, Loïc, Villiéras, Jean
Format: Article
Language:English
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Summary:The conjugate addition of magnesium cuprates to 2-silyloxycyclopentenecarboxylates leads, after desilylation, to 5-substituted-2-hydroxycyclopentanecarboxylates in high yields and diastereoselectivities. The 2-silyloxy derivatives avoid the formation of the SN 2′ reaction by-products. No loss of selectivity is also observed when a catalytic amount of cuprous salt is used. Conjugate addition of magnesium cuprates to 2-silyloxycyclopentenecarboxylates leads, after desilylation, to 5-substituted-2-hydroxycyclopentanecarboxylates in high yields and diastereoselectivities.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(96)01386-X