A highly enantioselective synthesis of tetrahydroindolizines by catalytic multicomponent cycloaddition reactions of diazoacetate, pyridine, and alkenyloxindole was developed. Under the relay catalysis, involving an achiral iron(III) catalyst and chiral N,N'-dioxide-scandium(III) complex, a series of tetrahydroindolizines bearing different substituents were obtained in moderate to high yields (up to 99 %) with excellent diastereo- and enantioselectivities (up to >19:1 d.r., 99 % ee).

Asymmetric Synthesis of Tetrahydroindolizines by Bimetallic Relay Catalyzed Cycloaddition of Pyridinium Ylides

https://nottingham-repository.worktribe.com/preview/895221/ol-2017-03252_accepted_combined.pdf

Iron-Catalyzed Indolizine Synthesis from Pyridines, Diazo Compounds, and Alkynes.

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2017

This study presents a convenient synthesis of pyrrolo[1,2- a]quinolines and pyrrolo[2,1- a]isoquinolines with simple quinolines or isoquinolines and Morita-Baylis-Hillman carbonates in the presence of copper acetate. A range of functionalized benzoindolizines could be assembled through an SN2'/deprotonation/1,5-electrocyclization/oxidation cascade pathway in a one-step process.

Synthesis of Benzoindolizines through 1,5-Electrocyclization/Oxidation Cascades

A novel copper-catalyzed [3 + 2] cycloaddition reaction of alkynes with nitrile oxides generated in situ from the coupling reaction of copper carbene and nitroso radical has been developed. The thr...

Copper-Catalyzed Cascade Cyclization Reactions of Diazo Compounds with tert-Butyl Nitrite and Alkynes: One-Pot Synthesis of Isoxazoles.

The Cu-catalyzed three-component reaction between quinolines, diazo compounds, and alkenes has been established for direct construction of indolizine derivatives via quinolinium ylides. This methodology is distinguished by the use of a commercially inexpensive catalyst and readily available starting materials, wide substrate scope, and operational simplicity.

Hongmei Sun

Papers

In Situ Generation of Quinolinium Ylides from Diazo Compounds: Copper-Catalyzed Synthesis of Indolizine.