Iterative Coupling of Two Different Enones by Nitromethane Using Bifunctional Thiourea Organocatalysts. Stereocontrolled Assembly of Cyclic and Acyclic Structures

Szilárd Varga, Gergely Jakab, Antal Csámpai, Tibor Soós

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

An organocatalytic iterative assembly line has been developed in which nitromethane was sequentially coupled with two different enones using a combination of pseudoenantiomeric cinchona-based thiourea catalysts. Application of unsaturated aldehydes and ketones in the second step of the iterative sequence allows the construction of cyclic syn-ketols and acyclic compounds with multiple contiguous stereocenters. The combination of the multifunctional substrates and ambident electrophiles rendered some organocatalytic transformations possible that have not yet been realized in bifunctional noncovalent organocatalysis.

Original languageEnglish
Pages (from-to)8990-8996
Number of pages7
JournalJournal of Organic Chemistry
Volume80
Issue number18
DOIs
Publication statusPublished - Sep 18 2015

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ASJC Scopus subject areas

  • Organic Chemistry

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