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Water overcomes methyl group directing effects in epoxide-opening cascades.

ABSTRACT: Water is an effective promoter of the endo-selective opening of trisubstituted epoxides, enabling related cascades leading to a variety of substituted ladder polyether structures. When used in conjunction with a tetrahydropyran-templated nucleophile, water can overcome the powerful electronic directing effect of a methyl substituent at either site of the epoxide, making water a uniquely versatile medium and promoter of epoxide opening.

SUBMITTER: Morten CJ

PROVIDER: S-EPMC2803343 | biostudies-literature | 2009 May

REPOSITORIES: biostudies-literature

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Water overcomes methyl group directing effects in epoxide-opening cascades.

Morten Christopher J CJ Jamison Timothy F TF

Journal of the American Chemical Society 20090501 19

Water is an effective promoter of the endo-selective opening of trisubstituted epoxides, enabling related cascades leading to a variety of substituted ladder polyether structures. When used in conjunction with a tetrahydropyran-templated nucleophile, water can overcome the powerful electronic directing effect of a methyl substituent at either site of the epoxide, making water a uniquely versatile medium and promoter of epoxide opening. ...[more]

PMID: 19402635

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