萘酚与硝基烯烃的有机催化不对称傅克烷基化/串联反应

Organocatalytic asymmetric Friedel-Crafts alkylation/cascade reactions of naphthols and nitroolefins.

作者信息

Liu Tian-Yu, Cui Hai-Lei, Chai Qian, Long Jun, Li Bang-Jing, Wu Yong, Ding Li-Sheng, Chen Ying-Chun

机构信息

Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.

出版信息

Chem Commun (Camb). 2007 Jun 14(22):2228-30. doi: 10.1039/b704925k. Epub 2007 May 4.

DOI:10.1039/b704925k

PMID:17534499

Abstract

The asymmetric Michael-type Friedel-Crafts reaction of naphthols and nitroolefins promoted by bifunctional thiourea-tertiary amine organocatalysts (up to 95% ee) was investigated; on simply extending the reaction time further cascade reactions could occur to generate enantiopure dimeric tricyclic 1,2-dihydronaphtho[2,1-b]furanyl-2-hydroxylamine derivatives.

摘要

研究了双功能硫脲-叔胺有机催化剂促进的萘酚与硝基烯烃的不对称迈克尔型傅克反应（对映体过量高达95%）；简单地进一步延长反应时间，可能会发生串联反应，生成对映体纯的二聚体三环1,2-二氢萘并[2,1-b]呋喃基-2-羟胺衍生物。