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Enantioselective Synthesis of Tropanes via [3+3] Annulation of Cyclic Azomethine Ylides with Substituted 2‐Vinylindoles and 2‐Vinylpyrroles
Author(s) -
Zheng Xing,
Yang WuLin,
Liu YangZi,
Wu ShuXiao,
Deng WeiPing
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800553
Subject(s) - annulation , chemistry , intramolecular force , enantioselective synthesis , indole test , pyrrole , tandem , ligand (biochemistry) , medicinal chemistry , combinatorial chemistry , catalysis , stereochemistry , organic chemistry , receptor , biochemistry , materials science , composite material
Abstract A novel strategy for constructing tropanes via [3+3] annulation of cyclic azomethine ylides with substituted 2‐vinylindoles and 2‐vinylpyrroles in the presence of in‐house Cu(II)/ N,O ‐ligand complex has been developed. The reaction was achieved via a tandem copper(II)‐catalyzed Michael addition/BF 3 ⋅ Et 2 O promoted intramolecular aza‐Friedel‐Crafts reaction of indoles or pyrroles with non‐activated ketimines, providing indole or pyrrole‐annulated tropanes in high yields (up to 87%) and excellent stereoselectivities (>99:1 dr in all cases, up to >99% ee).