Bismuth(III)-Catalyzed Sequential Enamine-Imine Tautomerism/2-Aza-Cope Rearrangement of Stable β-Enaminophosphonates: One-Pot Synthesis of β-Aminophosphonates

Ming Jin; Shi-Fu Yin; Shang-Dong Yang

doi:10.1021/acs.orglett.0c00796

Bismuth(III)-Catalyzed Sequential Enamine-Imine Tautomerism/2-Aza-Cope Rearrangement of Stable β-Enaminophosphonates: One-Pot Synthesis of β-Aminophosphonates

Org Lett. 2020 Apr 3;22(7):2811-2815. doi: 10.1021/acs.orglett.0c00796. Epub 2020 Mar 18.

Authors

Ming Jin¹, Shi-Fu Yin¹, Shang-Dong Yang^{1

2}

Affiliations

¹ State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.
² State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. China.

PMID: 32186884
DOI: 10.1021/acs.orglett.0c00796

Abstract

A novel catalytic tautomeric transformation of a β-enaminophosphoryl and 2-aza-Cope rearrangement sequence has been successfully applied to the one-pot synthesis of β-aminophosphonates with high efficiency and good tolerance. In this tandem reaction, Bi(OTf)₃ exhibits unique activities and promotes both of enamine-imine tautomerism and 2-aza-Cope rearrangement.

Publication types

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