[2+2] Cycloaddition reactions of imines with alkynyl selenides catalyzed by scandium triflate

It was found that a new reaction of imines with alkynyl selenides proceeded smoothly in the presence of a catalytic amount of Sc(OTf) 3 affording α,β-unsaturated selenylimidates. These reactions are assumed to proceed by a [2+2] cycloaddition of the imines to the alkynyl selenides to form azetine in...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2000-02, Vol.41 (6), p.945-947
Main Authors: Ma, Yun, Qian, Changtao
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:It was found that a new reaction of imines with alkynyl selenides proceeded smoothly in the presence of a catalytic amount of Sc(OTf) 3 affording α,β-unsaturated selenylimidates. These reactions are assumed to proceed by a [2+2] cycloaddition of the imines to the alkynyl selenides to form azetine intermediates, which are unstable and immediately fragment to the corresponding α,β-unsaturated selenylimidates.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)02178-4