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Stereoselective synthesis of highly functionalized alpha-diazo-beta-ketoalkanoates via catalytic one-pot Mukaiyama-Aldol reactions.

ABSTRACT: Methyl diazoacetoacetate undergoes zinc triflate catalyzed condensation with a broad selection of aldehydes to produce delta-siloxy-alpha-diazo-beta-ketoalkanoates in good yield, and delta-hydroxy-alpha-diazo-beta-ketoalkanoates are formed with high diastereoselectivity in reactions with alpha-diazo-beta-ketopentanoate promoted by dibutylboron triflate.

SUBMITTER: Zhou L

PROVIDER: S-EPMC2829718 | biostudies-literature | 2010 Feb

REPOSITORIES: biostudies-literature

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Stereoselective synthesis of highly functionalized alpha-diazo-beta-ketoalkanoates via catalytic one-pot Mukaiyama-Aldol reactions.

Zhou Lei L Doyle Michael P MP

Organic letters 20100201 4

Methyl diazoacetoacetate undergoes zinc triflate catalyzed condensation with a broad selection of aldehydes to produce delta-siloxy-alpha-diazo-beta-ketoalkanoates in good yield, and delta-hydroxy-alpha-diazo-beta-ketoalkanoates are formed with high diastereoselectivity in reactions with alpha-diazo-beta-ketopentanoate promoted by dibutylboron triflate. ...[more]

PMID: 20102172

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