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Equilibrium Asymmetric Induction in Sulfenamides—A Model for Asymmetric Synthesis
Author(s) -
Raban Morton,
Carlson Eric M.
Publication year - 1976
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.197600022
Subject(s) - chemistry , asymmetric induction , asymmetric carbon , diastereomer , sulfenamide , alkyl , equilibrium constant , atom (system on chip) , chiral auxiliary , stereochemistry , enantioselective synthesis , organic chemistry , catalysis , natural rubber , vulcanization , computer science , embedded system
Sulfenamides which contain an asymmetric carbon atom (stereostable chiral unit) in addition to the sulfenamide chiral axis (stereolabile chiral unit) exist as a mixture of diastereomers in equilibrium. The equilibrium constants, which can be measured by NMR spectroscopy, serve as a measure of the thermodynamic asymmetric induction of the stable chiral unit on the labile chiral unit. Two series of diastereomic sulfenamides (N‐alkyl‐N‐benzenesulfonyltrichloromethanesulfenamides and N‐alkyl‐N‐benzenesulfonyl‐2,4‐dinitrobenzenesulfenamides) were prepared and their equilibrium constants measured. The thermodynamic asymmetric induction in these systems is discussed and related to the asymmetric induction which occurs in asymmetric synthesis.