Chiral Phosphoric Acid-Catalyzed Enantioselective Construction of 2,3-Disubstituted Indolines | Zendy

WeiYang Ma | Zendy; Coralie Gelis | Zendy; Damien Bouchet | Zendy; Pascal Retailleau | Zendy; Xavier Moreau | Zendy; Luc Neuville | Zendy; Géraldine Masson | Zendy

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Chiral Phosphoric Acid-Catalyzed Enantioselective Construction of 2,3-Disubstituted Indolines

Author(s) -

WeiYang Ma,

Coralie Gelis,

Damien Bouchet,

Pascal Retailleau,

Xavier Moreau,

Luc Neuville,

Géraldine Masson

Publication year - 2021

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c03947

Subject(s) - chemistry , phosphoric acid , regioselectivity , enantioselective synthesis , cycloaddition , catalysis , combinatorial chemistry , organic chemistry

Highly enantio- and regioselective (3 + 2) formal cycloaddition of β-substituted ene- and thioenecarbamates as well as cyclic enamides with quinone diimides catalyzed by a BINOL- and SPINOL-derived phosphoric acid is reported. A wide variety of 2,3-disubstituted 2-aminoindolines, including polycyclic ones, were prepared in generally high yields (up to 98%) with moderate to complete diastereoselectivities and in most cases excellent enantioselectivities (up to 99% ee).

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