Enantioselective Gold-Catalyzed Pictet–Spengler Reaction | Zendy

Nicolas GlinskyOlivier | Zendy; Shengwen Yang | Zendy; Pascal Retailleau | Zendy; Vincent Gandon | Zendy; Xavier Guinchard | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Open Access

Enantioselective Gold-Catalyzed Pictet–Spengler Reaction

Author(s) -

Nicolas GlinskyOlivier,

Shengwen Yang,

Pascal Retailleau,

Vincent Gandon,

Xavier Guinchard

Publication year - 2019

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.9b03656

Subject(s) - chemistry , tryptamines , pictet–spengler reaction , enantioselective synthesis , indole test , yield (engineering) , functional group , catalysis , cationic polymerization , reaction conditions , tryptamine , combinatorial chemistry , organic chemistry , biochemistry , materials science , polymer , metallurgy

Cationic chiral Au(I) complexes catalyze asymmetric Pictet-Spengler reactions between tryptamines and arylaldehydes. The resulting tetrahydro-β-carbolines are obtained with wide functional group tolerance in high yield and with high enantioselectivities (up to 95%). Aldehydes bearing polar or protic functions are well tolerated. The reaction features a hitherto unknown C2-auration of the indole as the key step, supported by density functional theory calculations.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research