Base-catalyzed domino cyclization of acetylenes with ketones to functionalized cyclopentenes

Elena Yu Schmidt; Boris A Trofimov; Ivan A Bidusenko; Natalia A Cherimichkina; Igor' A Ushakov; Nadezhda I Protzuk; Yurii V Gatilov

doi:10.1021/ol501881e

Base-catalyzed domino cyclization of acetylenes with ketones to functionalized cyclopentenes

Org Lett. 2014 Aug 1;16(15):4040-3. doi: 10.1021/ol501881e. Epub 2014 Jul 23.

Authors

Elena Yu Schmidt¹, Boris A Trofimov, Ivan A Bidusenko, Natalia A Cherimichkina, Igor' A Ushakov, Nadezhda I Protzuk, Yurii V Gatilov

Affiliation

¹ A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences , 1 Favorsky Str., 664033 Irkutsk, Russia.

PMID: 25055028
DOI: 10.1021/ol501881e

Abstract

Acetylene reacts with methylaryl(hetaryl)ketones in the presence of 6.5 mol % KOH in DMSO to give diastereoselectively in single operationally functionalized cyclopentenes. This domino cyclization involving two molecules of acetylene and two molecules of ketone proceeds with the formation of four C-C bonds. The complementary assembly of the cyclopentenes with similar functionalities from acetylenes and 1,5-diketones has been developed.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Catalysis
Combinatorial Chemistry Techniques
Cyclization
Cyclopentanes / chemical synthesis*
Cyclopentanes / chemistry
Ketones / chemical synthesis*
Ketones / chemistry*
Molecular Structure
Stereoisomerism

Substances

Alkynes
Cyclopentanes
Ketones