TY - JOUR
T1 - Diastereoselective Ugi reaction without chiral amines
T2 - the synthesis of chiral pyrroloketopiperazines
AU - Nenajdenko, Valentine G.
AU - Reznichenko, Alexander L.
AU - Balenkova, Elizabeth S.
N1 - Funding Information:
Financial support from Russian Science Support Foundation is gratefully acknowledged. The authors also thank Dr. A. S. Shashkov for the NMR spectra and Dr. B. V. Lokshin for the optical rotation measurements.
Copyright:
Copyright 2008 Elsevier B.V., All rights reserved.
PY - 2007/4/2
Y1 - 2007/4/2
N2 - The three-component Ugi reaction with chiral 2-(2-formyl-1H-pyrrol-1-yl)acetic acids prepared from natural l-aminoacids was investigated. The reaction opens a new route to chiral substituted pyrroloketopiperazines. One of the first examples of an asymmetric Ugi reaction without chiral amines is described. The reaction proceeds with moderate diastereoselectivity to give the target compounds in good yields. The scope and limitation of the approach are discussed.
AB - The three-component Ugi reaction with chiral 2-(2-formyl-1H-pyrrol-1-yl)acetic acids prepared from natural l-aminoacids was investigated. The reaction opens a new route to chiral substituted pyrroloketopiperazines. One of the first examples of an asymmetric Ugi reaction without chiral amines is described. The reaction proceeds with moderate diastereoselectivity to give the target compounds in good yields. The scope and limitation of the approach are discussed.
UR - http://www.scopus.com/inward/record.url?scp=33847293705&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2007.01.056
DO - 10.1016/j.tet.2007.01.056
M3 - Article
AN - SCOPUS:33847293705
VL - 63
SP - 3031
EP - 3041
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 14
ER -