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Thermodynamic asymmetric induction: a new approach to the development of rules for the determination of absolute configurations

✍ Scribed by Morton Raban; Christophe P. Moulin; Sanford K. Lauderback; Brian Swilley

Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
250 KB
Volume
25
Category
Article
ISSN
0040-4039

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✦ Synopsis

The absolute configurations of chiral primary amines can be determined using the optical rotations of the corresponding N-p-toluenesulfonyl-N-2,4-dinitrobenzensulfenyl derivatives.

Kinetic asymmetric induction has been used as the basis for numerous methods for the determination of absolute and relative configurations. 2 Successfully and commonly used methods based upon asymmetric synthesis and kinetic resolution have been embodied in such rules as Prelog's Rule, 3 Cram's Rule, 4 Horeau's Rule, 5 and others. 6 This paper outlines a strategy for development of similar rules based on thermodynamic asyrmnetric induction -l at stereolabile chiral units and describes one such rule employing the sulfenamide chiral axis.

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