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

作者信息

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

机构信息

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

出版信息

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

DOI:10.1021/ol0261478

PMID:12074684

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.

摘要