1237786-79-6

Upstream product

• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 58649-21-1 (E)-(3-chloroprop-1-en-1-yl)cyclohexane 
• 1427549-15-2 (S)-2-(4-cyclohexylhexa-1,5-dien-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 2043-61-0 cyclohexanecarbaldehyde 
• 105880-38-4 (1S)-1-cyclohexyl-2-propyn-1-ol 
• 53724-05-3 1-cyclohexyl-3-(trimethylsilyl)prop-2-yn-1-one 
• 1378870-78-0 (R)-hex-5-en-1-yn-3-ylcyclohexane 
• 1237786-89-8 tert-butyl (1-cyclohexylallyl) carbonate 
• 1169852-09-8 tert-butyl (E)-3-cyclohexyl-2-propenyl carbonate 

Downstream Products

• 139592-41-9 (2R)-2-cyclohexyl-1,4-butanediol 

Relevant academic research and scientific papers

Copper-Catalyzed Enantioselective Coupling between Allyl-boronates and Phosphates Using a Phenol-Carbene Chiral Ligand: Asymmetric Synthesis of Chiral Branched 1,5-Dienes

Details of the Cu-catalyzed enantioselective allyl-allyl coupling reaction between allylboronates and (Z)-allylic phosphates using a new chiral N -heterocyclic carbene (NHC) ligand containing a phenolic hydroxy group are presented. The copper catalysis delivers enantio-enriched chiral 1,5-dienes with a tertiary stereogenic center. Compatibility with various functional groups and the use of earth-abundant and relatively low-toxicity copper as a metal are attractive features of this protocol. The utility of the chiral phenol-NHC ligand for enantioselective copper catalysis with organoboron compounds is demonstrated and enantiodiscrimination models are discussed.

Copper-Catalyzed Enantioselective Allyl–Allyl Coupling between Allylic Boronates and Phosphates with a Phenol/N-Heterocyclic Carbene Chiral Ligand

Copper-catalyzed enantioselective allyl–allyl coupling between allylboronates and either Z-acyclic or cyclic allylic phosphates using a new chiral N-heterocyclic carbene ligand, bearing a phenolic hydroxy, is reported. This reaction occurs with exceptional SN2′-type regioselectivities and high enantioselectivities to deliver chiral 1,5-diene derivatives with a tertiary stereogenic center at the allylic/homoallylic position.

Catalytic enantioselective allyl-allyl cross-coupling with a borylated allylboronate

Catalytic enantioselective allyl-allyl cross-coupling of a borylated allylboronate reagent gives versatile borylated chiral 1,5-hexadienes. These compounds may be manipulated in a number of useful ways to give functionalized chiral building blocks for asymmetric synthesis.

Construction of 1,5-enynes by stereospecific Pd-catalyzed allyl-propargyl cross-couplings

The palladium-catalyzed cross-coupling of chiral propargyl acetates and allyl boronates delivers chiral 1,5-enynes with excellent levels of chirality transfer and can be applied across a broad range of substrates.

Pd-catalyzed enantioselective allyl-allyl cross-coupling

The Pd-catalyzed cross-coupling of allylic carbonates and allylB(pin) is described. The regioselectivity of this reaction is sensitive to the bite angle of the ligand, with small-bite-angle ligands favoring the branched substitution product. This mode of