Work

Transformation of N,N-Dimethylaniline N-Oxides into Diverse Tetrahydroquinoline Scaffolds via Formal Povarov Reactions

Year: 2018

Type: article

Abstract: A one-pot protocol for the assembly of diversely functionalized tetrahydro-, hexahydrofuro-, hexahydropyrano-, and tetrahydrobenzofuroquinolines from N, N -dimethylaniline N -oxides and various electron-rich olefins in a tandem Polonovski–Povarov sequence is reported. Following activation of the N–O bond with Boc 2 O, an exocyclic iminium ion is unveiled upon exposure to tin(IV) chloride. A formal inverse-electron-demand aza-Diels–Alder cyclization generates the tetrahydroquinoline core of 29 examples in up to 92% yield.

Source: Organic Letters

DOI: 10.1021/acs.orglett.8b02318

Authors: Timothy S. Bush, Glenn P. A. Yap, William J. Chain

Institution: University of Delaware

Language: English

Topic: Multicomponent Synthesis of Heterocycles

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green