Chemodivergent and Stereoselective Construction of gem-Difluoroallylic Amines from Masked Difluorodiazo Reagents

Jun-Liang Zeng; Yue Zhang; Meng-Meng Zheng; Zhi-Qi Zhang; Xiao-Song Xue; Fa-Guang Zhang; Jun-An Ma

doi:10.1021/acs.orglett.9b02989

Chemodivergent and Stereoselective Construction of gem-Difluoroallylic Amines from Masked Difluorodiazo Reagents

Org Lett. 2019 Oct 18;21(20):8244-8249. doi: 10.1021/acs.orglett.9b02989. Epub 2019 Sep 12.

Authors

Jun-Liang Zeng^{1

2}, Yue Zhang^{1

2}, Meng-Meng Zheng³, Zhi-Qi Zhang^{1

2}, Xiao-Song Xue³, Fa-Guang Zhang^{1

2}, Jun-An Ma^{1

2

3}

Affiliations

¹ Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Centre of Chemical Science & Engineering , Tianjin University , Tianjin 300072 P.R. China.
² Joint School of NUS & TJU , International Campus of Tianjin University , Fuzhou 350207 , P.R. China.
³ State Key Laboratory of Elemento-Organic Chemistry , Nankai University , Tianjin 300071 , P.R. China.

PMID: 31513413
DOI: 10.1021/acs.orglett.9b02989

Abstract

We report a general and efficient approach to construct achiral and chiral gem-difluoroallylic amines from a masked difluorodiazo reagent (PhSO₂CF₂CHN₂) and readily available imines. This facile protocol takes advantage of the phenylsulfonyl and diazo moieties as efficient activating and directing groups to assist difluoroalkyl incorporation and facilitate the chemodivergent and stereoselective formation of gem-difluoroallylic amines.