Phosphine-mediated [3+2] cycloaddition reactions of ethyl 5,5-diarylpenta-2,3,4-trienoates with arylmethylidenemalononitriles and N-tosylimines

Xiao-Yang Guan; Min Shi

doi:10.1021/jo802489t

Phosphine-mediated [3+2] cycloaddition reactions of ethyl 5,5-diarylpenta-2,3,4-trienoates with arylmethylidenemalononitriles and N-tosylimines

J Org Chem. 2009 Mar 6;74(5):1977-81. doi: 10.1021/jo802489t.

Authors

Xiao-Yang Guan¹, Min Shi

Affiliation

¹ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.

PMID: 19173598
DOI: 10.1021/jo802489t

Abstract

Ethyl 5,5-diarylpenta-2,3,4-trienoates were synthesized and utilized in the phosphine-mediated [3+2] cycloaddition reactions with arylmethylidenemalononitriles and N-tosylimines in the presence of tributylphosphine. These reactions provide an easy access to a variety of novel polysubstituted cyclopentenes or pyrrolidines in good to excellent yields under mild conditions.

Publication types

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

MeSH terms

Cyclization
Cyclopentanes / chemical synthesis*
Cyclopentanes / chemistry
Imines / chemistry*
Molecular Structure
Nitriles / chemistry*
Phosphines / chemistry*
Pyrrolidines / chemical synthesis*
Pyrrolidines / chemistry
Stereoisomerism
Tosyl Compounds / chemistry

Substances

Cyclopentanes
Imines
Nitriles
Phosphines
Pyrrolidines
Tosyl Compounds
phosphine