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

Author:
Foley, Corinne N., Leighton, James L.
Source:
Organic letters 2014 v.16 no.4 pp. 1180-1183
ISSN:
1523-7052
Subject:
aldehydes, chemical structure, oxidation
Abstract:
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.”
Agid:
5788268