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Synthetic studies and mechanistic insight in nickel-catalyzed [4+2+1] cycloadditions.

ABSTRACT: A new nickel-catalyzed procedure for the [4+2+1] cycloaddition of (trimethylsilyl)diazomethane with alkynes tethered to dienes has been developed. A broad range of unsaturated substrates participate in the sequence, and stereoselectivities are generally excellent. Stereochemical studies provided evidence for a mechanism that involves the [3,3] sigmatropic rearrangement of divinylcyclopropanes.

SUBMITTER: Ni Y

PROVIDER: S-EPMC2720272 | biostudies-literature | 2006 Mar

REPOSITORIES: biostudies-literature

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Synthetic studies and mechanistic insight in nickel-catalyzed [4+2+1] cycloadditions.

Ni Yike Y Montgomery John J

Journal of the American Chemical Society 20060301 8

A new nickel-catalyzed procedure for the [4+2+1] cycloaddition of (trimethylsilyl)diazomethane with alkynes tethered to dienes has been developed. A broad range of unsaturated substrates participate in the sequence, and stereoselectivities are generally excellent. Stereochemical studies provided evidence for a mechanism that involves the [3,3] sigmatropic rearrangement of divinylcyclopropanes. ...[more]

PMID: 16492045

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