113829-98-4

Upstream product

• 109-72-8 n-butyllithium 
• 930-68-7 cyclohexenone 
• 34948-25-9 n-butylcopper 
• 129380-08-1 (S)-N-methyl-1-phenyl-2-(piperidin-1-yl)ethanamine 
• 148054-62-0 (S)-N-methyl-1-phenyl-2-(4-methyl-1-piperidinyl)ethanamine 
• 693-04-9 butyl magnesium bromide 
• 39178-69-3 rac-3-butylcyclohexanone 
• 1728-18-3 dimethylacetal of cyclohexenone 
• 6301-49-1 3-butylcyclohexenone 
• 1119-90-0 di-n-butylzinc 
• 106-98-9 1-butylene 
• 72170-87-7 (+)-(2S)-N-[cyclohex-2-en-1-yliden]-2-(methoxymethyl)pyrrolidin-1-amine 
• 693-03-8 n-butyl magnesium bromide 
• 16807-60-6 3-methoxycyclohex-2-en-1-one 

Downstream Products

• 87759-33-9 (1S,3R)-3-n-butyl-cyclohexanol 
• 69824-94-8 (1S,3S)-trans-3-n-butylcyclohexanol 
• 87759-32-8 (1R,3R)-3-Butyl-cyclohexanol 

Relevant academic research and scientific papers

A new approach to switching of enantioselectivity in NHC-Cu-catalyzed conjugate addition of alkylzincs to cyclic enones

Conjugate addition of Et2Zn to 2-cyclohexen-1-one catalyzed by Cu(OTf)2 combined with an azolium salt derived from (S)-leucinol produced the corresponding (S)-adduct, while the use of Cu(acac)2 in combination with the same

New chiral ligands for the asymmetric copper catalyzed conjugate addition of grignard reagents to enones

The copper catalyzed conjugate addition of n-butyl Grignard to enones in the presence of chiral ferrocenyl phosphine oxazoline ligands has been studied and found to provide useful levels of asymmetric induction. A comparison of the ferrocene derived ligan

Asymmetric Conjugate Addition of Organomagnesium Cuprates Controlled by a Stoichiometric Amount of Chiral Phosphine

A dramatic reversal in the enantiofacial differentiation was observed in a chiral phosphine mediated organocuprate addition to cycloalkenone, providing S- and R-product in up to 98percent ee by using magnesium- and lithium cuprate, respectively.

Catalytic asymmetric conjugate addition of Grignard reagents mediated by copper(I)-chiral bidentate phosphine complex

A catalytic amount of a chiral phosphine I-copper iodide complex catalyzes the conjugate addition of organomagnesium chlorides to cycloalkenones and pentenolide to give the corresponding addition products in 94-72% ee.

Enantioselective 1,4-Addition of Aliphatic Grignard Reagents to Enones Catalyzed by Readily Available Copper(I) Thiolates Derived from TADDOL

Two simple thiols derived from the parent TADDOL, α,α,α + ′,α + ′-tetraphenyl-2,2-dimethyl-1,3-dioxolan-4,5-dimethanol, are used to prepare Cu1 complexes C and D to catalyze (0.05 equiv.) 1,4-additions of Grignardreagents RMgCl to cyclic enones

Counterion Enhanced Organocatalysis: A Novel Approach for the Asymmetric Transfer Hydrogenation of Enones

We present a novel strategy for organocatalytic transfer hydrogenations relying on an ion-paired catalyst of natural l-amino acids as main source of chirality in combination with racemic, atropisomeric phosphoric acids as counteranion. The combination of a chiral cation with a structurally flexible anion resulted in a novel chiral framework for asymmetric transfer hydrogenations with enhanced selectivity through synergistic effects. The optimized catalytic system, in combination with a Hantzsch ester as hydrogen source for biomimetic transfer hydrogenation, enabled high enantioselectivity and excellent yields for a series of α,β-unsaturated cyclohexenones under mild conditions. Moreover, owing to the use of readily available and chiral pool-derived building blocks, it could be prepared in a straightforward and significantly cheaper way compared to the current state of the art.

CuI-Catalysed Enantioselective Alkyl 1,4-Additions to (E)-Nitroalkenes and Cyclic Enones with Phosphino-Oxazoline Ligands

Catalytic enantioselective conjugate additions of simple alkyl groups to nitroalkenes or cyclic enones that result in the formation of tertiary C–C bonds are described. For these stereoselective addition reactions, new chiral phosphino-oxazoline ligands w

A convenient catalytic asymmetric conjugate addition reaction to enones using alkylzirconium reagents

Alkylzirconium reagents undergo highly enantioselective copper-catalysed 1,4-addition reaction to cyclic enones. These reactions use alkylmetal species generated in situ from alkenes and the Schwartz reagent, and do not require premade organometallic reag

Chiral hetero- and carbocyclic compounds from the asymmetric hydrogenation of cyclic alkenes

Several types of chiral hetero- and carbocyclic compounds have been synthesized by using the asymmetric hydrogenation of cyclic alkenes. N,P-Ligated iridium catalysts reduced six-membered cyclic alkenes with various substituents and heterofunctionality in good to excellent enantioselectivity, whereas the reduction of five-membered cyclic alkenes was generally less selective, giving modest enantiomeric excesses. The stereoselectivity of the hydrogenation depended more strongly on the substrate structure for the five- rather than the six-membered cyclic alkenes. The major enantiomer formed in the reduction of six-membered alkenes could be predicted from a selectivity model and isomeric alkenes had complementary enantioselectivity, giving opposite optical isomers upon hydrogenation. The utility of the reaction was demonstrated by using it as a key step in the preparation of chiral 1,3-cis-cyclohexane carboxylates. Copyright

Hydroxy-amide functionalized azolium salts for Cu-catalyzed asymmetric conjugate addition: Stereocontrol based on ligand structure and copper precatalyst

A series of hydroxy-amide functionalized azolium salts have been designed and synthesized for Cu-catalyzed asymmetric conjugate addition reaction. The (CH2)2-bridged hydroxy-amide functionalized azolium ligand precursors 2, in addition to the previously reported CH2-bridged azolium salts 1, have been prepared from readily available enantiopure β-amino alcohols. The combination of a Cu species with 1 or 2 efficiently promoted the 1,4-addition reaction of cyclic enones with dialkylzincs. For example, the reaction of 2-cyclohepten-1-one (17) with Bu2Zn in the presence of catalytic amounts of Cu(OTf)2 and 1 gave (S)-3-butylcycloheptanone (20) in 99% yield and 96% ee. On the other hand, when the reaction was carried out under the influence of Cu(OTf)2 combined with 2, (R)-20 in preference to (S)-20 was obtained in 98% yield and 80% ee. In this manner, the enantioselecvity was switched by controlling the structure of chiral ligand. Additionally, the reversal of enantioselectivity was also achieved by changing the Cu precatalyst from Cu(OTf)2 to Cu(acac)2 with the same ligand. The combination of Cu(acac) 2 with CH2-bridged azolium salt 1 in the reaction of 17 with Bu2Zn led to formation of (R)-20 as a major product in 55% yield and 80% ee. This result was in contrast to the Cu(OTf)2/1 catalytic system, where the 1,4-adduct with opposite configuration was obtained. Moreover, use of the Cu(acac)2/2 catalytic system produced (S)-20, while (R)-20 was formed by the Cu(OTf)2/2 catalytic system. Thus, it was found that either varying the linker of the chiral ligands or changing the counterion of Cu species between a OTf and acac ligand initially on the metal led to dual enantioselective control in the 1,4-addition reaction.