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Stereoelectronic Effects and Chiral Recognition, II. Kinetic and Thermodynamic Control in the Formation of Chiral Thioacetals and Chiral Thioethers

✍ Scribed by Noe, Christian R. ;Knollmiiller, Max ;Ziebarth-Schroth, Irene ;Letschnig, Marion

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
568 KB
Volume
1996
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The ratio of diastereomers obtained from chiral thiols 2 was shown to be time‐dependent both in thioacetal formation with lactol 1 (diastereomers 3/4) and in 1,4‐addition to nitrostyrene 5 (diastereomers 6/7, 8/9). An interpretation based on stereoelectronic effects is presented to explain the similarity of the reaction pathways in both reactions.

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