Diastereoselective Ugi reaction without chiral amines: the synthesis of chiral pyrroloketopiperazines

Valentine G. Nenajdenko; Alexander L. Reznichenko; Elizabeth S. Balenkova

doi:10.1016/j.tet.2007.01.056

Diastereoselective Ugi reaction without chiral amines: the synthesis of chiral pyrroloketopiperazines

Valentine G. Nenajdenko^*, Alexander L. Reznichenko, Elizabeth S. Balenkova

^*Corresponding author for this work

Not published at VTT

Moscow State University (MSU)

Research output: Contribution to journal › Article › Scientific › peer-review

51 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	3031-3041
Number of pages	11
Journal	Tetrahedron
Volume	63
Issue number	14
DOIs	https://doi.org/10.1016/j.tet.2007.01.056
Publication status	Published - 2 Apr 2007
MoE publication type	A1 Journal article-refereed

Funding

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.

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10.1016/j.tet.2007.01.056

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title = "Diastereoselective Ugi reaction without chiral amines: the synthesis of chiral pyrroloketopiperazines",

abstract = "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.",

author = "Nenajdenko, {Valentine G.} and Reznichenko, {Alexander L.} and Balenkova, {Elizabeth S.}",

note = "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.",

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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.

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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.

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DO - 10.1016/j.tet.2007.01.056

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SP - 3031

EP - 3041

JO - Tetrahedron

JF - Tetrahedron

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ER -

Diastereoselective Ugi reaction without chiral amines: the synthesis of chiral pyrroloketopiperazines

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