Premium
Highly Enantioselective Synthesis of a 2,3‐Dihydroindole Mediated by N ‐Methylephedrine
Author(s) -
Vijn Robert Jan,
Speckamp W. Nico,
de Jong Bart S.,
Hiemstra Henk
Publication year - 1984
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.198401651
Subject(s) - enantioselective synthesis , catalysis , chemistry , stereochemistry , organic chemistry
Cyclization of the prochiral starting material 1 to the almost enantiomerically pure product 2, R = n ‐Pr , proceeded in the presence of the chiral catalyst formed from n ‐BuLi and N ‐methylephedrine 3 . (+)‐ 3 leads to (−)‐ 2 and (−)‐ 3 to (+)‐ 2 (>95% ee ). However, this result was not achieved with other substituents R in 1 .