67647-93-2

Upstream product

• 1199-95-7 1-(trimethylstannyl)-2-phenylethyne 
• 2043-61-0 cyclohexanecarbaldehyde 
• 345659-66-7 [(E)-1-(Chloro-phenyl-methyl)-2-cyclohexyl-vinyl]-triethyl-silane 
• 4361-25-5 3-cyclohexylprop-2-ynal 
• 615253-68-4 1-(1-cyclohexyl-3-phenyl-prop-2-ynyl)-pyrrolidine 
• 1228107-91-2 (3-cyclohexyl-3-benzyloxyprop-1-ynyl)benzene 
• 1422177-18-1 (S)-1-((S)-1-cyclohexyl-3-phenylprop-2-yn-1-yl)-2-(pyrrolidin-1-ylmethyl)pyrrolidine 
• 34266-29-0 N′-(cyclohexylmethylene)-4-methylbenzenesulfonohydrazide 
• 536-74-3 phenylacetylene 
• 82166-21-0 methyl cyclohexane 
• 100-52-7 benzaldehyde 
• 7436-90-0 2,2-dibromostyrene 
• 1512864-19-5 2,2'-(cyclohexylmethylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 
• 51207-66-0 (S)-2-(1-pyrrolidinylmethyl)pyrrolidine 

Downstream Products

• 1380239-79-1 (S,E)-2-cyclohexyl-4-phenylbut-3-en-1-ol 

Relevant academic research and scientific papers

Negishi Coupling for Highly Selective Syntheses of Allenes via Ligand Effect and Mechanistic Study via SAESI-MS/MS

β-H elimination is an intrinsic problem in transition metal-catalyzed reactions. We describe herein an interesting ligand effect for Et2Zn acting as either ethyl provider or H provider, respectively: by applying SPhos or Gorlos-Phos as the liga

Room Temperature Allenation of Terminal Alkynes with Aldehydes

A gold-catalyzed room temperature allenation of terminal alkynes (ATA) with aldehydes affording 1,3-disubstituted allenes with diverse functional groups has been developed by identifying a gold(I) catalyst and an amine. The practicality of this reaction has been demonstrated by a ten gram-scale synthesis and the synthetic potentials have been demonstrated via various transformations and formal total synthesis of (?)-centrolobine. Mechanistic studies revealed that the gold catalyst, the aldehyde effect, the fluoroalkyl hydroxyl solvent (TFE or HFIP) and the structure of amine are vital in this room temperature ATA reaction.

Copper-Catalyzed 1,1-Boroalkylation of Terminal Alkynes: Access to Alkenylboronates via a Three-Component Reaction

A copper-catalyzed three-component reaction of terminal alkynes, diazo compounds, and B2pin2 to prepare trisubstituted alkenylboronates has been developed. This difunctionalization of alkynes selectively occurs at the terminal carbon atom and proceeds via

PROCESS FOR SYNTHESIZING HIGHLY OPTICALLY ACTIVE 1,3-DISUBSTITUTED ALLENES

The present invention relates to a process for efficiently synthesizing highly optically active 1,3-disubstituted allenes, i.e., a one-step process for preparing highly optically active 1,3-disubstituted allenes by using a functionalized terminal alkyne,

SAMDI Mass Spectrometry-Enabled High-Throughput Optimization of a Traceless Petasis Reaction

Development of the self-assembled monolayer/MALDI mass spectrometry (SAMDI) platform to enable a high-throughput optimization of a traceless Petasis reaction is described. More than 1800 unique reactions were conducted simultaneously on an array of self-assembled monolayers of alkanethiolates on gold to arrive at optimized conditions, which were then successfully transferred to the solution phase. The utility of this reaction was validated by the efficient synthesis of a variety of di- and trisubstituted allenes.

A new protocol for nickel-catalysed regio- and stereoselective hydrocyanation of allenes

Regio- and stereoselective hydrocyanation under nickel catalysis is described. This report shows that allenyl C-C double bonds are discriminated and converted to the corresponding carbonitriles as a single product. The key functionalities for achieving high regio- and stereocontrol are aryl and cyclopropyl groups in the substrates. This journal is

Gold(III)-catalyzed enynamine-cyclopentadiene cycloisomerization with chirality transfer: An experimental and theoretical study indicating involvement of dual au(iii) push-pull assisted cis - Trans isomerism

A synthetic approach for asymmetric ring-fused cyclopentadienes (Cps) with a chiral carbon at the ring junction has been established from chiral enynamines by achiral Au(III) catalysis. On the basis of experimental and theoretical data, the proposed mechanistic pathway from enynamines to Cps occurs via a Au(III) ene cis-trans isomerization step. Computational studies at DFT and NEVPT2 levels advocate that the cis-trans isomerization step proceeds via a dual Au(III) push-pull assisted intermediate with a low computed rotation barrier. The chirality transfer occurs through a helical-shaped transition state with allenic character. The scope of the catalysis encompasses sterically bulky enynamines including terpene natural products.

Zinc salt promoted diastereoselective synthesis of chiral propargylamines using chiral piperazines and their enantioselective conversion into chiral allenes

Zinc chloride catalyzed reactions of chiral piperazine derivatives 4a-d with 1-alkynes and aldehydes give chiral propargylamines in 67-95 % yields with up to 99:1 dr. The chiral propargylamines are converted into chiral allenes by using zinc bromide in sh

Palladium(0)-catalyzed cross-coupling of 1,1-diboronates with vinyl bromides and 1,1-dibromoalkenes

Palladium-catalyzed cross-coupling reactions of 1,1-diboronates with vinyl bromides and dibromoalkenes were found to afford 1,4-dienes and allenes, respectively. These reactions utilize the high reactivities of both 1,1-diboronates and allylboron intermediates generated in the initial coupling.

Studies on ZnBr2-mediated synthesis of axially chiral aryl-substituted allenes from terminal alkynes, aromatic aldehydes and (S)-α,α-diphenylprolinol

The studies on the ZnBr2-mediated synthesis of axially chiral aryl-substituted allenes from terminal alkynes, aromatic aldehydes, and commercially available chiral amine (S)-α,α-diphenylprolinol were conducted. Axially chiral aryl-substituted a