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The Synthesis of C-2 Symmetry Diesters of (3r,4r)-Ttfol through a Green and Stereoselective (2r,3r)-Taddol Rearrangement

, , , , , and . Tetrahedron-Asymmetry, 26 (23): 1341-1347 (2015)
DOI: 10.1016/j.tetasy.2015.10.014

Abstract

An efficient, green, and atom economic methodology for the stereoselective synthesis of C-2 symmetry (3R,4R)-TTFOL diester derivatives has been developed. The procedure occurs through a (2R,3R)-TADDOL dioxolane cleavage and rearrangement under mild conditions by its reaction with a carboxylic acid in the presence of TFAA/H3PO4 without the need for an inert atmosphere to give generally high yields.

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