Beyond the Roche Ester: A New Approach to Polypropionate Stereotriad Synthesis | Zendy

Corinne N. Foley | Zendy; James L. Leighton | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Open Access

Beyond the Roche Ester: A New Approach to Polypropionate Stereotriad Synthesis

Author(s) -

Corinne N. Foley,

James L. Leighton

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol500051e

Subject(s) - stereocenter , chemistry , rhodium , sequence (biology) , combinatorial chemistry , catalysis , scalability , organic chemistry , stereochemistry , enantioselective synthesis , computer science , biochemistry , database

An efficient, step-economical, and scalable approach to the synthesis of polypropionate stereotriads has been developed. Either 2-butyne or propyne is subjected to rhodium-catalyzed silylformylation and in situ crotylation of the resulting aldehydes. Tamao oxidation under either "standard" conditions or "aprotic" conditions then delivers the completed stereotriads in a three-step, two-pot sequence. In contrast to the classical Roche ester approach, the α-stereocenter is obtained for "free."

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research