Premium
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.