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Stereoselective synthesis of quaternary carbons via the dianionic Ireland-Claisen rearrangement.

ABSTRACT: A dianionic Ireland-Claisen rearrangement of chiral, nonracemic ?-methyl-?-hydroxy allylic esters has been developed that proceeds with high diastereoselectivity and provides products containing three contiguous stereogenic carbons, including a quaternary center. The potential utility of the rearrangement for complex molecule synthesis is also demonstrated.

SUBMITTER: Crimmins MT

PROVIDER: S-EPMC4018138 | biostudies-literature | 2014 May

REPOSITORIES: biostudies-literature

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Stereoselective synthesis of quaternary carbons via the dianionic Ireland-Claisen rearrangement.

Crimmins Michael T MT Knight John D JD Williams Philip S PS Zhang Yan Y

Organic letters 20140415 9

A dianionic Ireland-Claisen rearrangement of chiral, nonracemic α-methyl-β-hydroxy allylic esters has been developed that proceeds with high diastereoselectivity and provides products containing three contiguous stereogenic carbons, including a quaternary center. The potential utility of the rearrangement for complex molecule synthesis is also demonstrated. ...[more]

PMID: 24735235

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