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Stereoelectronic Effects and Chiral Recognition, II. Kinetic and Thermodynamic Control in the Formation of Chiral Thioacetals and Chiral Thioethers
Author(s) -
Noe Christian R.,
Knollmiiller Max,
ZiebarthSchroth Irene,
Letschnig Marion
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960622
Subject(s) - diastereomer , chemistry , lactol , thioacetal , chiral auxiliary , kinetic control , stereochemistry , computational chemistry , organic chemistry , enantioselective synthesis , acetal , lactone , catalysis
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.