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

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

Downstream Products

• 16538-48-0 (Z)-1-cyclohexanyl-hex-1-ene 
• 192993-16-1 C₂₆H₄₁BO₂ 
• 120312-94-9 C₁₈H₃₃BO 
• 152192-50-2 C₂₅H₃₉BO₂ 
• 240405-71-4 allenyldicyclohexylborane 
• 273753-67-6 C₃₃H₄₈BNO₄S₂ 

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.

Hydroboration with haloborane/trialkylsilane mixtures

Trialkylsilanes or dialkylsilanes react rapidly with boron trichloride in the absence of ethereal solvents or other nucleophiles to form unsolvated dichloroborane. If no substrate is present, dichloroborane disproportionates to trichloroborane and two geo