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Regiochemical control in the metal-catalyzed transposition of allylic silyl ethers.

ABSTRACT: A novel mode of regiochemical control over the allylic [1,3]-transposition of silyloxy groups catalyzed by Re2O7 has been developed. This strategy relies on a cis-oriented vinyl boronate, generated from the Alder-ene reaction of homoallylic silyl ethers and alkynyl boronates, to trap out the allylic hydroxyl group. The resulting cyclic boronic acids are excellent partners for cross-coupling reactions. High chirality transfer is observed for the rearrangement of enantioenriched allylic silyl ethers.

SUBMITTER: Hansen EC

PROVIDER: S-EPMC2528283 | biostudies-literature | 2006 Jun

REPOSITORIES: biostudies-literature

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Regiochemical control in the metal-catalyzed transposition of allylic silyl ethers.

Hansen Eric C EC Lee Daesung D

Journal of the American Chemical Society 20060601 25

A novel mode of regiochemical control over the allylic [1,3]-transposition of silyloxy groups catalyzed by Re2O7 has been developed. This strategy relies on a cis-oriented vinyl boronate, generated from the Alder-ene reaction of homoallylic silyl ethers and alkynyl boronates, to trap out the allylic hydroxyl group. The resulting cyclic boronic acids are excellent partners for cross-coupling reactions. High chirality transfer is observed for the rearrangement of enantioenriched allylic silyl ethe ...[more]

PMID: 16787071

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