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Silylene-mediated ring contraction of homoallylic ethers to form allylic silanes.

ABSTRACT: (-)-Isopulegol derivatives undergo a ring contraction under silylene-mediated conditions to provide cyclopentane products. Silylene transfer to other homoallylic ethers did not provide the ring contraction products. Allylic silane products were elaborated to determine the stereochemical course of the ring contraction reaction. A mechanism for the transformation is proposed.

SUBMITTER: Bourque LE

PROVIDER: S-EPMC2749648 | biostudies-literature | 2009 Sep

REPOSITORIES: biostudies-literature

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Silylene-mediated ring contraction of homoallylic ethers to form allylic silanes.

Bourque Laura E LE Haile Pamela A PA Woerpel K A KA

The Journal of organic chemistry 20090901 18

(-)-Isopulegol derivatives undergo a ring contraction under silylene-mediated conditions to provide cyclopentane products. Silylene transfer to other homoallylic ethers did not provide the ring contraction products. Allylic silane products were elaborated to determine the stereochemical course of the ring contraction reaction. A mechanism for the transformation is proposed. ...[more]

PMID: 19681592

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