Study of chiral β-enaminones prepared from pyrrolidine, cytisine, salsoline and 2-amino-1-(4-nitrophenyl)propane-1,3-diol: resolution of salsoline via diastereomeric modified carane-type β-enaminones

A series of novel optically active β-enaminones have been prepared regio- and stereoselectively from primary and secondary amines (pyrrolidine, cytisine salsoline and 2-amino-1-(4-nitrophenyl)propane-1,3-diol) and (+)-3-carene-derived β-chlorovinylketone. Resolution of the isoquinoline alkaloid sals...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron: asymmetry 2003-01, Vol.14 (2), p.233-238
Main Authors: Popov, Sergey A., Gatilov, Yuri V., Rybalova, Tatjana V., Tkachev, Alexey V.
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:A series of novel optically active β-enaminones have been prepared regio- and stereoselectively from primary and secondary amines (pyrrolidine, cytisine salsoline and 2-amino-1-(4-nitrophenyl)propane-1,3-diol) and (+)-3-carene-derived β-chlorovinylketone. Resolution of the isoquinoline alkaloid salsoline has been demonstrated as well as isolation of a single diastereomeric adduct from racemic 2-amino-1-(4-nitrophenyl)propane-1,3-diol. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(02)00781-4