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Modular Catalytic Synthesis of 3‐Amino‐3‐aryl‐2‐oxindoles: Rh Catalysis with Isatin‐Derived N ‐Boc‐Protected Ketimines
Author(s) -
Marques Carolina S.,
Burke Anthony J.
Publication year - 2016
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.201501399
Subject(s) - isatin , chemistry , catalysis , enantioselective synthesis , aryl , amino acid , combinatorial chemistry , functional group , organic chemistry , biochemistry , alkyl , polymer
Chiral 3‐amino‐3‐aryloxindoles are important biologically active compounds. Using a catalytic modular approach, 31 new 3‐amino‐3‐aryl‐2‐oxindoles were prepared by a simple Rh‐catalysed addition of arylboronic acids to isatin‐derived N ‐Boc‐protected ketimines (Boc = tert‐ butoxycarbonyl). A low catalyst loading of 3 mol‐% was used, and the reaction showed a wide scope with high functional‐group compatibility, and gave good yields. We report the first catalytic enantioselective reactions with this substrate. Deprotection of the Boc group was easily accomplished in good yields.