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Insect Desaturases as Unique Analytical Tools To Unravel the Stereochemical Course of the Reduction of Vicinal Ditosylates with Lithium Aluminum Deuteride
Author(s) -
Navarro Isabel,
Fabrias Gemma,
Camps Francisco
Publication year - 1999
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/(sici)1521-3773(19990115)38:1/2<164::aid-anie164>3.0.co;2-m
Subject(s) - vicinal , walden inversion , toluene , chemistry , sulfonate , sulfonyl , lithium (medication) , inversion (geology) , lithium atom , computational chemistry , stereochemistry , organic chemistry , ion , sodium , medicine , paleontology , alkyl , structural basin , biology , endocrinology , ionization
Care is advisable in the reduction of vicinal sulfonate esters with LiAlD 4 , since the reaction takes an unexpected stereochemical course: whereas in the substitiution of one of the tosylate (Ts) groups an inversion of configuration at the C atom occurs, the other is substituted with retention of configuration. The latter can best be explained by a double inversion with participation of the neighboring group (see scheme). Ts= toluene‐4‐sulfonyl.