Title
|
|
|
|
Indium(III)-catalyzed tandem synthesis of 2-alkynyl-3,3-dichloropyrrolidines and their conversion to 3-chloropyrroles
| |
Author
|
|
|
|
| |
Abstract
|
|
|
|
The synthetic utility of electron-deficient alpha,alpha,gamma-trichloroaldimines was demonstrated by an indium(III) triflate-catalyzed cascade reaction with terminal alkynes allowing one to rapidly and selectively access 2-alkynyl-3,3-dichloropyrrolidines in good to excellent yields. The reaction proceeds in a single synthetic operation via an addition of acetylenes to alpha,alpha,gamma-trichloroaldimines, followed by a spontaneous cyclization of the in situ formed trichloropropargylic amines. The dichloromethylene moiety of the aldimine acts as an activating group to accomplish this transformation under very mild conditions. A broad variety of both aryl and alkyl acetylenes, as well as primary and secondary nitrogen substituents in the imine are well tolerated. The dichloromethylene group, which is conserved in the 2-alkynylpyrrolidine enhances the synthetic value of these pyrrolidines and allowed their conversion to (E/Z)-2-alkenyl-3-chloropyrroles by a base induced monodechlorination. |
| |
Language
|
|
|
|
English
| |
Source (journal)
|
|
|
|
RSC advances
| |
Publication
|
|
|
|
2015
| |
ISSN
|
|
|
|
2046-2069
| |
DOI
|
|
|
|
10.1039/C4RA14214D
| |
Volume/pages
|
|
|
|
5
:14
(2015)
, p. 10139-10151
| |
ISI
|
|
|
|
000348144100008
| |
Full text (Publisher's DOI)
|
|
|
|
| |
|