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

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

Research output: Contribution to journalArticleScientificpeer-review

45 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 languageEnglish
Pages (from-to)3031-3041
Number of pages11
JournalTetrahedron
Volume63
Issue number14
DOIs
Publication statusPublished - 2 Apr 2007
MoE publication typeA1 Journal article-refereed

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