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Beneficial Effect of ortho ‐Methoxy Groups in the Asymmetric Ring Opening of meso Epoxides with Silicon Tetrachloride Catalyzed by Chiral ortho ‐Methoxyphenyldiazaphosphonamide Lewis Bases Response to the Communication by G. Buono et al.
Author(s) -
Denmark Scott E.,
Wynn Thomas,
Jellerichs Bradley G.
Publication year - 2001
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 - 10.1002/1521-3773(20010618)40:12<2255::aid-anie2255>3.0.co;2-3
Subject(s) - enantioselective synthesis , cyclooctene , silicon tetrachloride , epoxide , ring (chemistry) , catalysis , chemistry , lewis acids and bases , yield (engineering) , medicinal chemistry , silicon , group (periodic table) , stereochemistry , organic chemistry , materials science , metallurgy
The reported ability of chiral phosphonamide 1 to effect the enantioselective opening of meso epoxides with silicon tetrachloride has not withstood experimental verification by Denmark's group. Having reexamined the ring‐opening of cyclooctene oxide (see scheme), Denmark and co‐workers found a serious discrepancy between their results (81–83 % recovery of the epoxide and an essentially racemic product) and those reported by Buono et al. (77 % yield and >99 % ee ).