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N-heterocyclic carbene-initiated alpha-acylvinyl anion reactivity: additions of alpha-hydroxypropargylsilanes to aldehydes.

ABSTRACT: Highly substituted alpha,beta-unsaturated ketones are prepared by the N-heterocyclic carbene-initiated addition of alpha-hydroxypropargylsilanes to aldehydes. This strategy serves as a highly efficient alternative to the standard Morita-Baylis-Hillman (MBH) approaches for these types of compounds. In contrast to the MBH reaction, different substitution in the beta-position of the product (R1) can be accommodated in moderate to excellent yields with a high degree of control over the resulting alkene.

SUBMITTER: Reynolds TE

PROVIDER: S-EPMC2987273 | biostudies-literature | 2007 Jun

REPOSITORIES: biostudies-literature

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N-heterocyclic carbene-initiated alpha-acylvinyl anion reactivity: additions of alpha-hydroxypropargylsilanes to aldehydes.

Reynolds Troy E TE Stern Charlotte A CA Scheidt Karl A KA

Organic letters 20070601 13

Highly substituted alpha,beta-unsaturated ketones are prepared by the N-heterocyclic carbene-initiated addition of alpha-hydroxypropargylsilanes to aldehydes. This strategy serves as a highly efficient alternative to the standard Morita-Baylis-Hillman (MBH) approaches for these types of compounds. In contrast to the MBH reaction, different substitution in the beta-position of the product (R1) can be accommodated in moderate to excellent yields with a high degree of control over the resulting alk ...[more]

PMID: 17539656

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