One-Pot Cascade Transformations of Zinc Trifluorodiazoethylide and α,β-Unsaturated Enones: Access to Trifluoromethylated Polycyclic Pyrazolines

Shuang Qin; Yan Zheng; Fa-Guang Zhang; Jun-An Ma

doi:10.1021/acs.orglett.7b01362

One-Pot Cascade Transformations of Zinc Trifluorodiazoethylide and α,β-Unsaturated Enones: Access to Trifluoromethylated Polycyclic Pyrazolines

Org Lett. 2017 Jul 7;19(13):3406-3409. doi: 10.1021/acs.orglett.7b01362. Epub 2017 Jun 14.

Authors

Shuang Qin¹, Yan Zheng¹, Fa-Guang Zhang¹, Jun-An Ma¹

Affiliation

¹ Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Tianjin University, and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Tianjin 300072, P. R. China.

PMID: 28613890
DOI: 10.1021/acs.orglett.7b01362

Abstract

One-pot cascade transformations are developed that involve [3 + 2] cycloaddition/Michael/aldol and [3 + 2] cycloaddition/double 1,2-addition reactions of zinc trifluorodiazoethylide with various α,β-unsaturated enones. The protocol provides straightforward access to trifluoromethyl-substituted polycyclic pyrazolines with high chemo-, regio-, and diastereoselectivity.

Publication types

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