36140-19-9

Usage

Uses

CHLORODICYCLOHEXYLBORANE is used as a reagent for various chemical reactions due to its reducing properties and ability to form stable complexes with carbonyl compounds.
Used in Aldol Addition Reactions:
CHLORODICYCLOHEXYLBORANE is used as a reducing agent for aldol addition reactions, which are important in the synthesis of complex organic molecules and natural products. It helps in the formation of carbon-carbon bonds and provides good yields and selectivity.
Used in Mukaiyama Aldol Addition:
In the Mukaiyama aldol addition, CHLORODICYCLOHEXYLBORANE is used as a Lewis acid catalyst to promote the reaction between silyl enol ethers and aldehydes, leading to the formation of β-hydroxy carbonyl compounds with high diastereoselectivity.
Used in Microwave Assisted Ring Closing Metathesis Reactions:
CHLORODICYCLOHEXYLBORANE is employed as a reducing agent in microwave-assisted ring-closing metathesis reactions, which are used to form cyclic compounds with the help of microwave irradiation. This method allows for faster reaction times and improved yields.
Used in C-Alkylation of Aromatic Aldimines:
CHLORODICYCLOHEXYLBORANE is used as a reagent for the C-alkylation of aromatic aldimines, a reaction that involves the formation of a carbon-carbon bond between an aromatic imine and an alkyl group, leading to the synthesis of various organic compounds.
Used in Reversible Ketone-Ketone Aldol Reactions:
In reversible ketone-ketone aldol reactions, CHLORODICYCLOHEXYLBORANE acts as a reducing agent to facilitate the formation of carbon-carbon bonds between ketones, which can be reversed under certain conditions, allowing for the synthesis of complex molecules with controlled selectivity.
Used in Synand Anti-Stereoselective Aldol Reactions:
CHLORODICYCLOHEXYLBORANE is used as a reagent in synand anti-stereoselective aldol reactions, which involve the formation of carbon-carbon bonds with specific stereochemistry. This allows for the synthesis of enantiomerically pure compounds, which are important in the pharmaceutical and agrochemical industries.

InChI:InChI=1/C12H22BCl/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h11-12H,1-10H2

Upstream product

• 110-83-8 cyclohexene 
• 90083-63-9 C₆H₅C(P(C₆H₅)3)B(C₆H₁₁)2 
• 542-18-7 cyclohexyl chloride 
• 165612-94-2 bis(pentafluorophenyl)borohydride 
• 1568-65-6 bis(cyclohexanyl)borane 
• 617-86-7 triethylsilane 
• 592-41-6 1-hexene 
• 10294-34-5 boron trichloride 
• 55382-85-9 B-iododicyclohexylborane 
• 10025-91-9 antimony(III) chloride 
• 63348-81-2 monochloroborane dimethyl sulfide complex 
• 1088-01-3 tricyclohexylborane 

Downstream Products

• 273753-67-6 C₃₃H₄₈BNO₄S₂ 
• 28047-28-1 cyclohexyl-(p-methylphenyl)-methanol 
• 106165-42-8 (4-chlorophenyl)-cyclohexyl methanol 
• 94823-85-5 cyclohexyl(naphthalen-1-yl)methanol 
• 106166-01-2 (4-bromophenyl)-cyclohexyl methanol 
• 491589-41-4 (4S,5R,6R)-4-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-cyclohexyl-6-isopropenyl-5-methyl-[1,3,2]dioxaborinane 
• 639087-36-8 C₄₁H₆₉BO₇Si 
• 120312-96-1 C₁₇H₃₁BO 
• 140112-11-4 C₁₉H₃₃BO 

Relevant academic research and scientific papers

Novel Synthesis of the Monochloroborane-Dimethyl Sulphide Complex via the Reaction of Borane-Dimethyl Sulphide with Trichloromethane

Monochloroborane-dimethyl sulphide, BH2Cl*SMe2, is formed in essentially quantitative yield upon reflux of an equimolar mixture of borane-dimethyl sulphide, BH3*SMe2, and tetrachloromethane; it can be used directly for production of dialkylchloroboranes b

Nickel-Catalyzed Alkyl-Alkyl Cross-Electrophile Coupling Reaction of 1,3-Dimesylates for the Synthesis of Alkylcyclopropanes

Cross-electrophile coupling reactions of two Csp3-X bonds remain challenging. Herein we report an intramolecular nickel-catalyzed cross-electrophile coupling reaction of 1,3-diol derivatives. Notably, this transformation is utilized to synthesize a range of mono- and 1,2-disubstituted alkylcyclopropanes, including those derived from terpenes, steroids, and aldol products. Additionally, enantioenriched cyclopropanes are synthesized from the products of proline-catalyzed and Evans aldol reactions. A procedure for direct transformation of 1,3-diols to cyclopropanes is also described. Calculations and experimental data are consistent with a nickel-catalyzed mechanism that begins with stereoablative oxidative addition at the secondary center.

Diastereoselectivity in the boron aldol reaction of α-alkoxy and α,β-bis-alkoxy methyl ketones

In this work, using DFT calculations, we investigated the 1,4 and 1,5 asymmetric induction in boron enolate aldol reactions of α-alkoxy and α,β-bisalkoxy methyl ketones. We evaluated the steric influence of alkyl substituents at the α position and the stereoelectronic influence of the oxygen protecting groups at the α and β positions. Theoretical calculations revealed the origins of the 1,4 asymmetric induction in terms of the nature of the β-substituent. The synergistic effect between the α,β-syn and α,β-anti-bisalkoxy stereocenters was elucidated. In the presence of the β-alkoxy center, the reaction proceeds through the Goodman-Paton 1,5-stereoinduction model, experiencing a minor influence of the α-alkoxy center.

Interactions of C?F Bonds with Hydridoboranes: Reduction, Borylation and Friedel–Crafts Alkylation

The stoichiometric reactions of the alkylfluorides 1-fluoroadamantane (Ad-F), fluorocyclohexane (Cy-F), 1-fluoropentane (Pent-F) and benzyl fluorides with secondary boranes pinacolborane (HBpin), catecholborane (HBcat), 9-borabicyclo(3.3.1)nonane (9-BBN)

Total regio- and diastereocontrol in the aldol reactions of dienolborinates

It is reported that appropriate dienolborinates can provide access to both diastereomers of 2-(hydroxymethyl)but-3-enoates through exclusive α-regiocontrol in a non-vinylogous pathway. Contrary to previous reports in which dialkylchloroboranes failed to enolize propanoates, acidity-enhanced but-3-enoates readily undergo enolization, offering unprecedented control over the formation of these valuable synthons. The first example of an aldol reaction in the presence of a phosphine-borane adduct is also reported.

Total synthesis of aplyronine C

A highly stereocontrolled total synthesis of the cytotoxic marine macrolide aplyronine C is described. The route exploits aldol methodology to install the requisite stereochemistry and features a crucial boron-mediated aldol coupling of an N-vinylformamide-bearing methyl ketone with a macrocyclic aldehyde to introduce the full side chain. The synthesis of two novel C21-C34 side chain analogs is also reported.

Process for total synthesis of pladienolide B and pladienolide D

[Problems to be Solved] To provide an effective process for total synthesis of pladienolide B and pladienolide D having excellent anti-tumor activity and to provide useful intermediates in the above-described process. [Measure for Solving the Problem] A process for producing a compound represented by Formula (11): wherein P1, P7, P8, P9 and R1 are the same as defined below, characterized by including reacting a compound represented by Formula (12): wherein P7 means a hydrogen atom or a protecting group for hydroxy group; R1 means a hydrogen atom or a hydroxy group, with a compound represented by Formula (13): wherein P1 means a hydrogen atom or a protecting group for hydroxy group; P8 means a hydrogen atom, an acetyl group or a protecting group for hydroxy group; P9 means a hydrogen atom or a protecting group for hydroxy group; or P8 and P9 may form together a group represented by a formula: wherein R5 means a phenyl group which may have a substituent, in the presence of a catalyst.

Toward the combinatorial synthesis of polyketide libraries: Asymmetric aldol reactions with α-chiral aldehydes on solid support

(Matrix presented) The viability of performing stereocontrolled aldol additions with α-chiral aldehydes attached by a silyl linker to a hydroxymethylpolystyrene resin is demonstrated for boron and titanium enolates. Subsequent ketone reduction and manipul

Chiral dihydroxyacetone equivalents in synthesis: Rapid assembly of styryl 1,2-polyols as an entry to the styryllactone family of natural products

A rapid entry to the polyol framework of the styryllactone family of natural products is reported. The key steps are two highly diastereoselective boron-mediated aldol reactions of a chiral dihydroxyacetone equivalent followed by a 1,3-anti or 1,3-syn-selective reduction. In addition, Evans-Tishchenko reduction of the cyclic aldol products effected an equilibration to the 1,2-syn aldol product before 1,3-anti selective reduction.

Bis(bicyclo(2.2.2)octyl)haloboranes

A novel class of enolboration reagents represented by the formula wherein each R is the same or different alkyl or cycloalkyl, B is boron, X is halo, R' is lower alkyl and / indicates that R2 BX is preferably employed in the presence of R'3 N are disclosed. Methods of enolborating a wide variety of organic carbonyl compounds are also provided. Further, new bis(bicyclo[2.2.2.]octyl)haloboranes are efficacious for enolboration.