Phosphine-Catalyzed Asymmetric [4+2] Annulation of Vinyl Ketones with Oxindole-Derived α,β-Unsaturated Imines: Enantioselective Syntheses of 2′,3′-Dihydro-1′H-spiro[indoline-3,4′-pyridin]-2-ones

A novel asymmetric [4+2] annulation of vinyl ketones with oxindole‐derived α,β‐unsaturated imines has been developed in the presence of a multifunctional thiourea‐phosphine catalyst derived from a natural amino acid, providing the first phosphine‐catalyzed enantioselective synthesis of 2′,3′‐dihydro...

Full description

Saved in:
Bibliographic Details
Published in:Advanced synthesis & catalysis 2013-11, Vol.355 (17), p.3351-3357
Main Authors: Zhang, Xiao-Nan, Chen, Gen-Qiang, Dong, Xiang, Wei, Yin, Shi, Min
Format: Article
Language:English
Subjects:
asymmetric [4+2] annulation
chiral phosphines
organocatalysts
spirooxindoles
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:A novel asymmetric [4+2] annulation of vinyl ketones with oxindole‐derived α,β‐unsaturated imines has been developed in the presence of a multifunctional thiourea‐phosphine catalyst derived from a natural amino acid, providing the first phosphine‐catalyzed enantioselective synthesis of 2′,3′‐dihydro‐1′H‐spiro[indoline‐3,4′‐pyridin]‐2‐ones in good yields with excellent stereoselectivities under mild conditions.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201300828