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.

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

The invention discloses an indolizine derivative and a preparation method thereof. A cheap copper compound is taken as a catalyst, a pyridine derivative, an olefinic derivative and a heavy nitrogen derivative are taken as reactants, and the catalyst and the reactants are subjected to cyclization reaction in a mixed solvent to obtain a product indolizine. The catalyst prepared with the method disclosed by the invention is cheap, can be easily obtained, is high in reaction activity, is moderate in reaction conditions, only needs to be carried out in the air, has a wide primer applicable range and is convenient in aftertreatment, and a final product can be obtained through simple column chromatography after reaction is finished. A target product has the advantages of high yield, simple preparation process, environment protection and wide raw material resource. The indolizine derivative conforms to the requirement and the direction of modern green chemistry development and has a potential industrial application value.

Yanwei Zhao

Papers

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

Indolizine derivative and preparation method thereof