61153-36-4

Upstream product

• 931-48-6 2-cyclohexylacetylene 
• 1191-15-7 diisobutylaluminium hydride 

Downstream Products

• 1365918-08-6 (E)-benzyl 2-(2-cyclohexylvinyl)-4-oxopiperidine-1-carboxylate 
• 121598-55-8 (E)-3-cyclohexyl-N-phenylacrylamide 
• 91801-77-3 C₁₂H₁₆ 
• 1309474-25-6 (R)-(E)-3-(2-cyclohexylvinyl)-3-methylcyclohexanone 

Relevant academic research and scientific papers

Palladium-Catalyzed Carbonylative Coupling of Aryl Iodides with Alkenylaluminum Reagents

A highly reactive catalytic system for the carbonylative coupling of aryl iodides with alkenylaluminum reagents has been developed. Various β-substituted γ,δ-unsaturated ketones were produced under mild conditions in good to excellent yields even under ppm level of palladium catalyst. Notably, this also represents the first example on carbonylative transformation of alkenylaluminum compounds. Additionally, by the addition of zinc salt, the selectivity of the product can be modified.

An Alumino-Mannich Reaction of Organoaluminum Reagents, Silylated Amines, and Aldehydes

A multi-component coupling using organoaluminum reagents, silylated amines, and aldehydes results in the formation of tertiary amines. Both alkenyl- and alkylaluminum reagents undergo reaction with iminium ion substrates for which the corresponding Petasis borono-Mannich reactions are unsuccessful.

Tandem Hydroalumination/Cu-Catalyzed Asymmetric Vinyl Metalation as a New Access to Enantioenriched Vinylcyclopropane Derivatives

Herein, we report the first enantio- and diastereoselective addition of stereodefined vinyl organometallic reagents to cyclopropenes. The operationally simple tandem hydroalumination and copper-catalyzed vinylmetalation allows for the unique access of a diverse set of enantioenriched vinylcyclopropane derivatives.

Nucleophilic β-alkenylation of N-alkoxyenamines: An umpolung strategy for the preparation of β,γ-unsaturated ketones

An umpolung strategy has been developed for the synthesis of β,γ-unsaturated ketones utilizing nucleophilic β-alkenylation of N-alkoxyenamines, which are prepared in situ from ketones and isoxazolidine, with alkenyl aluminum reagents. Various β,γ-unsatura

A multicomponent Ni-, Zr-, and Cu-catalyzed strategy for enantioselective synthesis of alkenyl-substituted quaternary carbons

The availability of enantiomerically enriched carbonyl-containing compounds is essential to the synthesis of biologically active molecules. Since catalytic enantioselective conjugate addition (ECA) reactions directly generate the latter valuable class of molecules, the design and development of such protocols represents a compelling objective in modern chemistry. Herein, we disclose the first solution to the problem of ECA of alkenyl groups to acyclic trisubstituted enones, an advance achieved by adopting an easily modifiable and fully catalytic approach. The requisite alkenylaluminum reagents are synthesized with exceptional site- and/or stereoselectivity by a Ni-catalyzed hydroalumination process, and the necessary enones are prepared through a site- and stereoselective zirconocene-catalyzed carboalumination/acylation reaction. The all-catalytic procedure is complete within four hours, furnishing the desired products in up to 77 % overall yield and 99:1 enantiomeric ratio. One-two-three punch: Ni-catalyzed alkyne hydroalumination, Zr-catalyzed alkyne carbometalation/acylation, and Cu-catalyzed enantioselective conjugate addition are combined for accessing acyclic organic molecules that contain an alkene-substituted quaternary carbon stereogenic center. The entire process takes less than four hours and affords products in up to 77 % overall yield and 99:1 enantiomeric ratio. Copyright

Copper-catalyzed asymmetric conjugate addition of alkenyl- and alkylalanes to α,β-unsaturated lactams

Alkenyl and alkyl groups have been successfully introduced to six-membered α,β-unsaturated lactams via a copper-catalyzed asymmetric 1,4-addition of the corresponding alanes. Moderate to good yields and good to excellent enantioselectivities are achieved by using a combination of the very cheap copper(II) naphthenate and a readily available phosphine amine ligand. The creation of an all-carbon quaternary stereogenic center, via Michael addition to a trisubstituted conjugated lactam, is also disclosed for the first time.

α-Selective Ni-catalyzed hydroalumination of aryl- and alkyl-substituted terminal alkynes: Practical syntheses of internal vinyl aluminums, halides, or boronates

A method for Ni-catalyzed hydroalumination of terminal alkynes, leading to the formation of α-vinylaluminum isomers efficiently (>98% conv in 2-12 h) and with high selectivity (95% to >98% α), is described. Catalytic α-selective hydroalumination reactions proceed in the presence of a reagent (diisobutylaluminum hydride; dibal-H) and 3.0 mol % metal complex (Ni(dppp)Cl2) that are commercially available and inexpensive. Under the same conditions, but with Ni(PPh3)2Cl2, hydroalumination becomes highly β-selective, and, unlike uncatalyzed transformations with dibal-H, generates little or no alkynylaluminum byproducts. All hydrometalation reactions are reliable, operationally simple, and practical and afford an assortment of vinylaluminums that are otherwise not easily accessible. The derived α-vinyl halides and boronates can be synthesized through direct treatment with the appropriate electrophiles [e.g., Br 2 and methoxy(pinacolato)boron, respectively]. Ni-catalyzed hydroaluminations can be performed with as little as 0.1 mol % catalyst and on gram scale with equally high efficiency and selectivity.