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Silver-Catalyzed Aldehyde Olefination Using Siloxy Alkynes.

ABSTRACT: We describe the development of a silver-catalyzed carbonyl olefination employing electron rich siloxy alkynes. This process constitutes an efficient synthesis of trisubstituted unsaturated esters, and represents an alternative to the widely utilized Horner-Wadsworth-Emmons reaction. Excellent diastereoselectivities are observed for a range of aldehydes using either 1-siloxy-1-propyne or 1-siloxy-1-hexyne. This mild catalytic process also enables chemoselective olefination of aldehydes in the presence of either ester or ketone functionality. Furthermore, since no by-products are generated, this catalytic process is perfectly suited for development of sequential reactions that can be carried out in a single flask.

SUBMITTER: Sun J

PROVIDER: S-EPMC3837490 | biostudies-literature | 2010 Mar

REPOSITORIES: biostudies-literature

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Silver-Catalyzed Aldehyde Olefination Using Siloxy Alkynes.

Sun Jianwei J Keller Valerie A VA Meyer S Todd ST Kozmin Sergey A SA

Advanced synthesis & catalysis 20100301 5

We describe the development of a silver-catalyzed carbonyl olefination employing electron rich siloxy alkynes. This process constitutes an efficient synthesis of trisubstituted unsaturated esters, and represents an alternative to the widely utilized Horner-Wadsworth-Emmons reaction. Excellent diastereoselectivities are observed for a range of aldehydes using either 1-siloxy-1-propyne or 1-siloxy-1-hexyne. This mild catalytic process also enables chemoselective olefination of aldehydes in the pre ...[more]

PMID: 24273478

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