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

DOI: 10.1016/0040-4039(96)01386-X

Source and publish data:

Tetrahedron Letters p. 6323 - 6326 (1996)

Update date:2022-08-16

Topics:

Authors:

Dambrin, Valery

Villieras, Monique

Moreau, Celine

Amri, Hassen

Toupet, Loic

Villieras, Jean

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Article abstract of DOI:10.1016/0040-4039(96)01386-X

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 SN₂' reaction by-products. No loss of selectivity is also observed when a catalytic amount of cuprous salt is used.

Full text of DOI:10.1016/0040-4039(96)01386-X

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