Organocatalytic Asymmetric Synthesis of Trifluoromethylated Tetrahydrocarbazoles by a Vinylogous Michael/Aldol Formal [4+2] Annulation | Zendy

Jafari Ehsan | Zendy; Chauhan Pankaj | Zendy; Kumar Mukesh | Zendy; Chen XiangYu | Zendy; Li Sun | Zendy; von Essen Carolina | Zendy; Rissanen Kari | Zendy; Enders Dieter | Zendy

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Organocatalytic Asymmetric Synthesis of Trifluoromethylated Tetrahydrocarbazoles by a Vinylogous Michael/Aldol Formal [4+2] Annulation

Author(s) -

Jafari Ehsan,

Chauhan Pankaj,

Kumar Mukesh,

Chen XiangYu,

Li Sun,

von Essen Carolina,

Rissanen Kari,

Enders Dieter

Publication year - 2018

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201800034

Subject(s) - stereocenter , chemistry , aldol reaction , annulation , organocatalysis , michael reaction , enantioselective synthesis , stereochemistry , organic chemistry , catalysis , combinatorial chemistry

A new protocol for the organocatalytic asymmetric synthesis of highly functionalized tetrahydrocarbazoles has been developed based on a vinylogous Michael/aldol reaction sequence between 3‐(trifluoroacetyl)‐2‐methyl‐indoles and enals. This formal [4+2] annulation occurs by cooperative catalysis between an achiral Brønsted base and a chiral secondary amine organocatalyst to afford tetrahydrocarbazole products bearing three vicinal stereocenters, including a trifluoromethylated tetrasubstituted stereocenter, in excellent yields, diastereo‐ and enantioselectivities.

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