I 2 ‐Induced Stereospecific Synthesis of 4‐Piperidones through Double Mannich Reaction and Tandem Cyclization

An I 2 ‐induced double Mannich reaction and tandem cyclization of imines and ketones was investigated for the synthesis of a series of 1,2,6‐triaryl‐4‐piperidones. During the process of cyclization, only one product was produced out of four possible 4‐piperidones. Two pathways involving the balance...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2011-03, Vol.2011 (9), p.1627-1631
Main Authors: Jia, Xiao‐Dong, Chen, Xiang‐Ning, Wang, Xiao‐E, Huo, Cong‐De, Wang, Wen‐Juan, Ren, Yan, Wang, Xi‐Cun
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:An I 2 ‐induced double Mannich reaction and tandem cyclization of imines and ketones was investigated for the synthesis of a series of 1,2,6‐triaryl‐4‐piperidones. During the process of cyclization, only one product was produced out of four possible 4‐piperidones. Two pathways involving the balance between chelation effects and hydrogen bonding were proposed to rationalize the formation of the products, which was supported by further investigation of the reaction between β‐aminoketones and imines.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201001607