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Stereoselective Synthesis of Trifluoromethyl Analogues of Polyhydroxypyrrolidines
Author(s) -
Khangarot Rama K.,
Kaliappan Krishna P.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201599
Subject(s) - chemistry , trifluoromethyl , stereoselectivity , nucleophile , molecule , organic chemistry , nucleophilic addition , fluorine , combinatorial chemistry , bond cleavage , stereochemistry , catalysis , alkyl
Incorporation of fluorine atoms into organic molecules significantly enhances many of their properties, such as solubility, metabolic stability, and bioavailability. Among organofluorine molecules, trifluoromethylated compounds play a unique and important role in agricultural and medicinal chemistry. An efficient strategy for the synthesis of a variety of trifluoromethylated polyhydroxypyrrolidines is described. This strategy involves a diastereoselective nucleophilic addition reaciton of trimethyl(trifluoromethyl)silane to sugar‐derived cyclic nitrones followed by reductive N–O bond cleavage and removal of benzyl groups.