title: Beyond the Roche ester: a new approach to polypropionate stereotriad synthesis.
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."
authors: Department of Chemistry, Columbia University , 3000 Broadway, Mail Code 3117, New York, New York 10027, United States.
authors: Corinne N
authors: CN
authors: Foley
authors: James L
authors: JL
authors: Leighton
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D004952:Esters; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D011422:Propionates / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000480:Alkynes; D004952:Esters; D011108:Polymers; D011422:Propionates; D012238:Rhodium