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Rhodium( I )‐Catalyzed [2+2+2] Cycloadditions with N‐Functionalized 1‐Alkynylamides: A Conceptually New Strategy for the Regiospecific Synthesis of Substituted Indolines
Author(s) -
Witulski Bernhard,
Stengel Thomas
Publication year - 1999
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/(sici)1521-3773(19990816)38:16<2426::aid-anie2426>3.0.co;2-y
Subject(s) - indoline , rhodium , acetylene , chemistry , catalysis , cycloaddition , combinatorial chemistry , indole test , stereochemistry , organic chemistry
The regiospecific introduction of substituents into the 4‐position of 2,3‐dihydroindoles (indolines), which is significant for the synthesis of various natural products and pharmaceuticals, was achieved by rhodium( I )‐catalyzed cyclotrimerizations of 1 with acetylene to give 2 . Up to four substituents can be introduced simultaneously into the indoline core by using this novel strategy. R=OH, OBzl, Otetrahydropyranyl, NHSO 2 C 6 H 4 CH 3 ; Ts=H 3 CC 6 H 4 SO 2 .