A Rh(II)-catalyzed multicomponent reaction by trapping an α-amino enol intermediate in a traditional two-component reaction pathway

Abstract

Rh(II)-catalyzed multicomponent reaction achieved to give α-amino-β-indole ketones by trapping α-amino enols with vinylimine ions.

An Overview of Rhodium‐Catalysed Multi‐Component Reactions

“…In 2017, Liu and co‐workers successfully trapped an in situ generated ylide or zwitterion from diazo compound and alcohol/amine/indole by electrophiles such as imines and aldehydes to produce α‐amino‐ß‐indole ketones . Interestingly, indoles with enhanced nucleophilicity at C 3 gave the multi‐component product, instead of a Davies's [3+2] cycloaddition product.…”

A DFT calculation-inspired Rh(i)-catalyzed reaction via suppression of α-H shift in α-alkyldiazoacetates

“…The investigations were conducted using the M06/Lanl2dz+6-31G* method 10 , 11 in Gaussian 09 software, 12 which is commonly used for describing metal carbene reactions. 11 , 13 The frequency analyses were performed on optimized structures in the gas phase to verify whether they were transition states or stable structures. The solvent effect of CH 2 Cl 2 was evaluated using the integral equation formalism model (IEFPCM).…”

One-pot synthesis of multi-substituted conjugated dienones by trapping allene carbocations with active ylides

“…Based on the continuous attention to the diverse transformations of active ylide intermediates, 10 we envisaged that an allene carbocation might be captured by the active oxonium ylides, which in situ are generated from alcohols and diazo compounds to promote an unprecedent transformation (Scheme 1b, designed). Oxonium ylides are highly reactive and readily deliver O–H insertion products via the 1,2-proton shift.…”