Stereoselective synthesis of polysubstituted 2,5-dihydrofurans from reaction of 1,4-dilithio-1,3-dienes with aldehydes

Jinglong Chen; Qiuling Song; Pixu Li; Hairong Guan; Xianglin Jin; Zhenfeng Xi

doi:10.1021/ol0261478

Stereoselective synthesis of polysubstituted 2,5-dihydrofurans from reaction of 1,4-dilithio-1,3-dienes with aldehydes

Org Lett. 2002 Jun 27;4(13):2269-71. doi: 10.1021/ol0261478.

Authors

Jinglong Chen¹, Qiuling Song, Pixu Li, Hairong Guan, Xianglin Jin, 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: 12074684
DOI: 10.1021/ol0261478

Abstract

[reaction: see text] Reaction of 1,4-dilithio-1,3-diene derivatives with 2 equiv of aldehydes affords polysubstituted 2,5-dihydrofurans in good to high yields with perfect regio- and stereoselectivities. Hexa-2,4-diene-1,6-dialcoholates are proposed as the first intermediates, which undergo a cyclization and subsequent elimination of Li(2)O to generate the 2,5-dihydrofuran derivatives.

Publication types

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

MeSH terms

Biological Factors / chemical synthesis
Butadienes / chemistry
Crystallography, X-Ray
Cyclization
Furans / chemical synthesis*
Lithium / chemistry
Molecular Structure
Organometallic Compounds / chemistry
Stereoisomerism

Substances

Biological Factors
Butadienes
Furans
Organometallic Compounds
Lithium