Gold and BINOL-Phosphoric Acid Catalyzed Enantioselective Hydroamination/N-Sulfonyliminium Cyclization Cascade | Zendy

Alex W. Gregory | Zendy; Pavol Jakubec | Zendy; Paul Turner | Zendy; Darren J. Dixon | Zendy

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Gold and BINOL-Phosphoric Acid Catalyzed Enantioselective Hydroamination/N-Sulfonyliminium Cyclization Cascade

Author(s) -

Alex W. Gregory,

Pavol Jakubec,

Paul Turner,

Darren J. Dixon

Publication year - 2013

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/ol401784h

Subject(s) - hydroamination , chemistry , phosphoric acid , enantioselective synthesis , catalysis , yield (engineering) , combinatorial chemistry , enantiomer , sulfonamide , cascade , organic chemistry , chromatography , materials science , metallurgy

A highly enantioselective hydroamination/N-sulfonyliminium cyclization cascade is reported using a combination of gold(I) and chiral phosphoric acid catalysts. An initial 5-exo-dig hydroamination and a subsequent phosphoric acid catalyzed cyclization process provide access to complex sulfonamide scaffolds in excellent yield and high enantiocontrol. The method can be extended to lactam derivatives, with excellent yields and enantiomeric excesses of up to 93% ee.

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