Asymmetric Dearomatization of β-Naphthols through a Bifunctional-Thiourea-Catalyzed Michael Reaction

Shou-Guo Wang; Xi-Jia Liu; Qun-Chao Zhao; Chao Zheng; Shao-Bo Wang; Shu-Li You

doi:10.1002/anie.201507998

Asymmetric Dearomatization of β-Naphthols through a Bifunctional-Thiourea-Catalyzed Michael Reaction

Angew Chem Int Ed Engl. 2015 Dec 1;54(49):14929-32. doi: 10.1002/anie.201507998. Epub 2015 Oct 14.

Authors

Shou-Guo Wang¹, Xi-Jia Liu¹, Qun-Chao Zhao¹, Chao Zheng¹, Shao-Bo Wang¹, Shu-Li You^{2

3}

Affiliations

¹ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/
² State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/. slyou@sioc.ac.cn.
³ Collaborative Innovation Center of Chemical Science and Engineering (Tianjin). slyou@sioc.ac.cn.

PMID: 26463712
DOI: 10.1002/anie.201507998

Abstract

An intermolecular asymmetric dearomatization reaction of β-naphthols with nitroethylene through a chiral-thiourea-catalyzed Michael reaction is described. Enantioenriched functionalized β-naphthalenones with an all-carbon quaternary stereogenic center could thus be easily constructed from simple naphthol derivatives in good yields and excellent enantioselectivity (up to 79% yield, 98% ee).

Keywords: Michael reaction; asymmetric dearomatization; naphthols; nitroethylene; organocatalysis.

Publication types

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