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Asymmetric Synthesis of Diarylmethyl Amines by Rhodium‐Catalyzed Asymmetric Addition of Aryl Titanium Reagents to Imines
Author(s) -
Hayashi Tamio,
Kawai Masahiro,
Tokunaga Norihito
Publication year - 2004
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200461338
Subject(s) - reagent , aryl , chemistry , isopropyl , catalysis , moiety , ring (chemistry) , combinatorial chemistry , rhodium , medicinal chemistry , organic chemistry , alkyl
A rational tuning of the arene sulfonamide moiety (by introducing isopropyl groups onto the phenyl ring) brought about high enantioselectivity in the asymmetric synthesis of diarylmethyl amines by the title reaction (see scheme). Ar 1 =4‐CF 3 C 6 H 4 , 4‐ClC 6 H 4 , 4‐FC 6 H 4 , 3‐MeOC 6 H 4 , 4‐MeOC 6 H 4 , 2‐MeC 6 H 4 , 1‐naphthyl, Ph; Ar 2 =Ph, 4‐FC 6 H 4 , 3‐MeOC 6 H 4 , 4‐MeOC 6 H 4 .