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Bi(OTf) 3 ‐Catalyzed Diastereoselective S N 1‐Type Reactions of Chiral Propargylic Acetates
Author(s) -
Rubenbauer Philipp,
Herdtweck Eberhardt,
Strassner Thomas,
Bach Thorsten
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200804025
Subject(s) - chemistry , selectivity , nucleophile , trimethylsilyl , catalysis , medicinal chemistry , alkane stereochemistry , stereochemistry , organic chemistry , molecule
Stereoelectronic factors are apparently responsible for the high selectivity observed in the title S N 1‐type reaction of acetates 1 in favor of the anti products 2 . The preferred conformation of the intermediate propargylic cations would lead to the syn product; however, a second conformation exists, in which the tert ‐butyl group adopts an antiperiplanar orientation with respect to the incoming nucleophile. Tf=trifluoromethanesulfonyl, TMS=trimethylsilyl.