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A general metal-free approach for the stereoselective synthesis of C-glycals from unactivated alkynes.

ABSTRACT: A novel metal-free strategy for a rapid and ?-selctive C-alkynylation of glycals was developed. The reaction utilizes TMSOTf as a promoter to generate in situ trimethylsilylacetylene for C-alkynylation. Thanks to this methodology, we can access C-glycosides in a single step from a variety of acetylenes , i.e., arylacetylenes and most importantly aliphatic alkynes.

SUBMITTER: Devari S

PROVIDER: S-EPMC4273296 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature

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A general metal-free approach for the stereoselective synthesis of C-glycals from unactivated alkynes.

Devari Shekaraiah S Kumar Manjeet M Deshidi Ramesh R Rizvi Masood M Shah Bhahwal Ali BA

Beilstein journal of organic chemistry 20141112

A novel metal-free strategy for a rapid and α-selctive C-alkynylation of glycals was developed. The reaction utilizes TMSOTf as a promoter to generate in situ trimethylsilylacetylene for C-alkynylation. Thanks to this methodology, we can access C-glycosides in a single step from a variety of acetylenes , i.e., arylacetylenes and most importantly aliphatic alkynes. ...[more]

PMID: 25550726

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