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Beyond the Roche ester: a new approach to polypropionate stereotriad synthesis
Corinne N Foley1, James L Leighton
1Department of Chemistry, Columbia University , 3000 Broadway, Mail Code 3117, New York, New York 10027, United States.
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."
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