Premium
Synthesis of a C–N Axially Chiral N ‐Arylisatin through Asymmetric Intramolecular N ‐Arylation
Author(s) -
Nakazaki Atsuo,
Miyagawa Keitaro,
Miyata Noriaki,
Nishikawa Toshio
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500593
Subject(s) - stereocenter , intramolecular force , chemistry , stereochemistry , axial symmetry , isatin , enantioselective synthesis , axial chirality , combinatorial chemistry , catalysis , organic chemistry , structural engineering , engineering
We describe the first synthesis of an enantiomerically pure C–N axially chiral N ‐arylisatin from the corresponding N ‐aryloxindole, which was synthesized by an asymmetric intramolecular Buchwald–Hartwig N ‐arylation. This novel isatin would be a potentially versatile synthetic intermediate for a variety of 3,3‐disubstituted oxindoles bearing a C3 stereogenic center.