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Chiral bifunctional sulfide-catalyzed asymmetric bromoaminocyclizations

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Title: Chiral bifunctional sulfide-catalyzed asymmetric bromoaminocyclizations
Authors: Nakamura, Takumi / Okuno, Ken / Kaneko, Kazuma / Yamanaka, Masahiro / Shirakawa, Seiji
Issue Date: 16-Apr-2020
Publisher: Royal Society of Chemistry
Citation: Organic & biomolecular chemistry, 18(17), pp.3367-3373; 2020
Abstract: A BINOL-derived chiral bifunctional sulfide catalyst bearing a phenylurea moiety was applied to enantioselective bromoaminocyclization reactions of 2-allylaniline derivatives, which provide optically active 2-substituted indoline products as important motifs for biologically active compounds. A protecting group on the nitrogen of the 2-allylaniline substrate was carefully optimized, and highly enantioselective reactions were achieved by employing thep-biphenylsulfonyl-protected substrates. The origin of the good level of enantioselectivity for the present bromoaminocyclization was also investigated on the basis of DFT calculations. The resultant optically active 2-(bromomethyl)indoline products could be transformed to various 2-substituted indolines with no loss of the optical purity.
URI: http://hdl.handle.net/10069/39998
ISSN: 14770520
DOI: 10.1039/D0OB00459F
Rights: © 2020 The Royal Society of Chemistry.
Type: Journal Article
Text Version: author
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/39998

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