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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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3993613 | PMC |
| http://dx.doi.org/10.1021/ol500051e | DOI Listing |
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