Chiral Binaphthyl Box-Copper-Catalyzed Enantioselective Tandem Michael–Ketalization Annulations for Optically Active Aryl and Heteroaryl Fused Bicyclicnonanes

The combination of chiral binaphthyl box-copper­(II) with triflimide (Tf2NH) was identified as an efficient catalytic system for the asymmetric Michael/ketalization of (E)-2-hydroxyaryl-2-oxobut-3-enoates or (E)-ethyl 4-(2-aminoaryl)-2-oxobut-3-enoates with pyrazolone derivatives. The corresponding...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2020-05, Vol.22 (10), p.3936-3941
Main Authors: Fan, Wei-Tai, Yang, Xiao-Peng, Lv, Hao-Peng, Wang, Xing-Wang, Wang, Zheng
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The combination of chiral binaphthyl box-copper­(II) with triflimide (Tf2NH) was identified as an efficient catalytic system for the asymmetric Michael/ketalization of (E)-2-hydroxyaryl-2-oxobut-3-enoates or (E)-ethyl 4-(2-aminoaryl)-2-oxobut-3-enoates with pyrazolone derivatives. The corresponding asymmetric tandem reactions provided a series of enantioenriched aryl and heteroaryl fused 2,8-O,O- or O,N-bicyclo­[3.3.1]­nonanes in high yields with excellent enantio- and diastereoselectivities.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01221