An Intramolecular [2 + 2] Cycloaddition of Ketenimines via Palladium-Catalyzed Rearrangements of N-Allyl-Ynamides

A cascade of Pd-catalyzed N-to-C allyl transfer–intramolecular ketenimine–[2 + 2] cycloadditions of N-allyl ynamides is described. This tandem sequence is highly stereoselective and the [2 + 2] cycloaddition could be rendered in a crossed or fused manner depending on alkene substitutions, leading to...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2012-06, Vol.14 (12), p.3214-3217
Main Authors: DeKorver, Kyle A, Hsung, Richard P, Song, Wang-Ze, Wang, Xiao-Na, Walton, Mary C
Format: Article
Language:English
Subjects:
Amides - chemistry
Bridged Bicyclo Compounds - chemistry
Catalysis
Cyclization
Ethylenes - chemistry
Imines - chemistry
Ketones - chemistry
Molecular Structure
Palladium - chemistry
Stereoisomerism
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 cascade of Pd-catalyzed N-to-C allyl transfer–intramolecular ketenimine–[2 + 2] cycloadditions of N-allyl ynamides is described. This tandem sequence is highly stereoselective and the [2 + 2] cycloaddition could be rendered in a crossed or fused manner depending on alkene substitutions, leading to bridged and fused bicycloimines.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol3013233