Acyl-lithiation of olefins: formation of cyclopentenones from 1-lithio-butadienes and CO

Qiuling Song; Zhiping Li; Jinglong Chen; Congyang Wang; Zhenfeng Xi

doi:10.1021/ol026977l

Acyl-lithiation of olefins: formation of cyclopentenones from 1-lithio-butadienes and CO

Org Lett. 2002 Dec 26;4(26):4627-9. doi: 10.1021/ol026977l.

Authors

Qiuling Song¹, Zhiping Li, Jinglong Chen, Congyang Wang, Zhenfeng Xi

Affiliation

¹ Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.

PMID: 12489946
DOI: 10.1021/ol026977l

Abstract

[reaction: see text] Intramolecular acyl-lithiation of C=C double bonds proceeds following carbonylation of 1-lithio-1,3-dienes with CO to afford 2- or 3-cyclopentenone derivatives in good to excellent yields after hydrolysis. Addition of electrophiles to the carbonylation reaction mixtures affords various multiply substituted cyclopentenones.