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Asymmetric Synthesis of 3‐Amino Oxindoles Using Isatin‐Derived N ‐Boc Ketimines with Activated Nitroolefin Catalyzed by Organocatalysts
Author(s) -
Choudhary Manoj K.,
Menapara Tusharkumar,
Tak Rajkumar,
Kureshy Rukhsana I.,
Khan Noorul H.
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201700032
Subject(s) - isatin , thiourea , yield (engineering) , catalysis , chemistry , organocatalysis , enantioselective synthesis , combinatorial chemistry , organic chemistry , medicinal chemistry , stereochemistry , materials science , metallurgy
Asymmetric synthesis of 3‐aminooxindole via aza‐MBH reaction by using isatin‐derived N ‐Boc ketimines with activated nitroolefin ( 2 and 3 ) is reported for the first time by using various organocatalysts where chiral thiourea‐based organocatalyst OC‐7 was found to be better catalyst to give the products in high yield with high diastereoselectivity (up to >99:1) and good enantioselectivity (up to 97:3 er). A probable mechanism for the formation of 3‐aminooxindole is established by 1 H & 13 C NMR studies.