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.
%0 Journal Article
%1 RN258
%A Costantino, A.R.
%A Schneider, M.G.M.
%A Galdamez, A.
%A Ocampo, R.A.
%A Mandolesi, S.D.
%A Koll, L.C.
%D 2015
%I 2015 Elsevier Ltd.
%J Tetrahedron-Asymmetry
%K analogs, anhydrides carboxylic-acids, derivatives, dqcauchile esterification, esters, in-situ, inhibitors, integrase ligands, taddol,
%N 23
%P 1341-1347
%R 10.1016/j.tetasy.2015.10.014
%T The Synthesis of C-2 Symmetry Diesters of (3r,4r)-Ttfol through a Green and Stereoselective (2r,3r)-Taddol Rearrangement
%U /brokenurl#<Go to ISI>://WOS:000366070000005
%V 26
%X 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.
@article{RN258,
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. },
added-at = {2019-12-04T03:57:35.000+0100},
author = {Costantino, A.R. and Schneider, M.G.M. and Galdamez, A. and Ocampo, R.A. and Mandolesi, S.D. and Koll, L.C.},
biburl = {https://www.bibsonomy.org/bibtex/2dba1a2a6fd448c7691006a8accf042ef/dqcauchile},
doi = {10.1016/j.tetasy.2015.10.014},
interhash = {50f3757aedce1e2560063211ce14e526},
intrahash = {dba1a2a6fd448c7691006a8accf042ef},
issn = {0957-4166},
journal = {Tetrahedron-Asymmetry},
keywords = {analogs, anhydrides carboxylic-acids, derivatives, dqcauchile esterification, esters, in-situ, inhibitors, integrase ligands, taddol,},
number = 23,
pages = {1341-1347},
publisher = {2015 Elsevier Ltd.},
timestamp = {2019-12-04T03:58:17.000+0100},
title = {The Synthesis of C-2 Symmetry Diesters of (3r,4r)-Ttfol through a Green and Stereoselective (2r,3r)-Taddol Rearrangement},
type = {Journal Article},
url = {/brokenurl#<Go to ISI>://WOS:000366070000005},
volume = 26,
year = 2015
}