109686-68-2

Upstream product

• 636-82-8 cyclohexene-1-carboxylic acid 
• 6832-87-7 2-bromo-N-methylaniline 
• 889102-86-7 (E)-1-(dimethylphenylsilanyl)-5-(2-iodo-1-methyl-1H-indol-3-yl)pent-1-en-3-ol 
• 603-76-9 1-methylindole 
• 75833-63-5 2-iodo-1-methyl-1H-indole 

Relevant academic research and scientific papers

Construction of Quaternary Stereocenters by Nickel-Catalyzed Heck Cyclization Reactions

A nickel-catalyzed Heck cyclization for the construction of quaternary stereocenters is reported. This transformation is demonstrated in the synthesis of 3,3-disubstituted oxindoles, which are prevalent motifs seen in numerous biologically active molecules. The method shows broad scope, proceeds in synthetically useful yields, and provides a rare means to construct stereochemically complex frameworks by nonprecious-metal catalysis.

Stereoselective synthesis of spirocyclic oxindoles based on a one-pot Ullmann coupling/Claisen rearrangement and its application to the synthesis of a hexahydropyrrolo[2,3-b]indole alkaloid

An efficient and convenient approach to the synthesis of spirocyclic oxindoles from iodoindoles has been developed. The most striking feature of this approach is that the sequential intramolecular Ullmann coupling and Claisen rearrangement proceeds in a one-pot manner to afford 3-spiro-2-oxindoles in good yield with excellent diastereoselectivity. Application of this one-pot reaction to chiral non-racemic tertiary alcohol substrates resulted in complete chirality transfer to the spirocyclic quaternary carbon. Using this method, asymmetric total synthesis of (-)-debromoflustramine B was accomplished.

Highly diastereoselective one-pot synthesis of spirocyclic oxindoles through intramolecular Ullmann coupling and Claisen rearrangement

(Chemical Equation Presented) An efficient and convenient approach to the synthesis of spirocyclic oxindoles from iodoindoles involves a sequential intramolecular C-O Ullmann coupling reaction and Claisen rearrangement (see scheme). The one-pot procedure affords 3-spiro-2-oxindoles in good yield with excellent diastereoselectivities.

Palladium complexes of phosphinamine ligands in the intramolecular asymmetric Heck reaction

The synthesis of two novel cyclisation substrates for the asymmetric intramolecular Heck reaction is reported. Their cyclisation, in addition to a known substrate for cis-decalin formation, were tested with palladium complexes of BINAP and heterobidentate oxazoline-containing ligands. In general BINAP provides a more active catalyst system for the range of substrates tested although excellent enantioselectivities of up to 85% were obtained with the P,N ligands studied. A trend was noted whereby the t-leucine-derived oxazoline ligands were more reactive and enantioselective than the valine-derived analogues. Similarly, the diphenylphosphinoferrocenyloxazoline ligands were more reactive and selective than the corresponding diphenylphosphinophenyloxazoline ligands.

Concise synthesis of tetrahydrophenanthridone by palladium reagent

Heck reaction of N-(2-halophenyl)-N-methyl-1-cyclohexene-1carboxamide (1) and 2-bromo-N-methyl-N-phenyl-1-cyclohexene-1-carboxamide (4) using a palladium reagent under several reaction conditions was examined. Reaction of 4 using Pd(OAc)2, DPPP, and Bu3P afforded tetrahydrophenanthridone (5) in excellent yield.