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Stereoselective Alkylation of Aromatic Compounds with Threonine Trifluoromethanesulfonates
Author(s) -
Effenberger Franz,
Weber Thomas
Publication year - 1987
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198701421
Subject(s) - diastereomer , threonine , chemistry , walden inversion , alkylation , carbocation , stereoselectivity , benzene , specific rotation , stereochemistry , organic chemistry , medicinal chemistry , catalysis , serine , enzyme
Complete retention of configuration at C‐2 and a surprising degree of retention (> 96% ee ) at C‐3 was observed upon reaction of the threonine derivatives (2 S ,3 R )‐ and (2 R ,3 S )‐ 1 with benzene. In the case of the allothrconine derivatives (2 S ,3 S )‐ and (2 R ,3 R )‐ 1 , on the other hand, 2 :3 mixtures of diastereomers result. This is ascribed to hindered rotation in the carbocation that is formed from the threonine derivatives.