63126-49-8

Upstream product

• 126308-99-4 4-(1-Cyclohexyl-pentyloxymethyl)-1,2-dimethoxy-benzene 
• 109-72-8 n-butyllithium 
• 110-62-3 pentanal 
• 2043-61-0 cyclohexanecarbaldehyde 
• 1920-90-7 tetra-n-butyl lead 
• 132841-63-5 (Z)-(1R,4R)-1-Cyclohexyl-4-(dimethyl-phenyl-silanyl)-pent-2-en-1-ol 
• 132841-63-5 (Z)-(1S,4R)-1-Cyclohexyl-4-(dimethyl-phenyl-silanyl)-pent-2-en-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 108-85-0 1-bromocyclohexane 
• 693-03-8 n-butyl magnesium bromide 
• 75-16-1 methylmagnesium bromide 
• 874964-01-9 1-cyclohexyl-1-(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)-methanol 
• 122-56-5 tributyl borane 
• 1144522-11-1 C₂₀H₃₁BO₅S 

Downstream Products

• 5445-35-2 1-cyclohexyl-1-pentanone 
• 1197170-98-1 C₁₃H₂₄O₂ 
• 93548-33-5 (S)-(-)-1-cyclohexylpentanol 

Relevant academic research and scientific papers

Catalytic asymmetric addition of aldehydes using organolithium reagents in the presence of commercial available chiral diol ligands

An efficient method for the catalytic asymmetric additions to aldehydes using organolithium reagents and titanium(IV) isopropoxide in the presence of commercially available and relatively inexpensive diol ligands, such as (S)-BINOL or D-TADDOL has been developed. Good to excellent yields (up to 92%) and enantioselectivities (up to 94%) of the corresponding secondary alcohol products can be obtained following a simple procedure at relatively mild reaction temperatures.

Synthesis of alcohols from m-fluorophenylsulfones and dialkylboranes: Application to the C14-C35 building block of E7389

The reaction of m-fluorophenylsulfone anions with dialkylboranes, followed by alkaline hydroperoxide oxidation, yields alcohols in high yields. Optimization of the process, scope and limitation, and application to the synthesis of one of the C14-C35 building blocks of E7389, a right half analogue of halichondrin B, are reported.

Catalytic enantioselective addition of MeMgBr and other Grignard reagents to aldehydes

Herein, we report an efficient catalyst for the challenging enantioselective addition of MeMgBr to aldehydes. Unprecedented yields and enantioselectivities are achieved in the reaction with a broad range of aldehydes. Moreover, a variety of Grignard reagents can be also added to aromatic and aliphatic aldehydes in good yields and enantioselectivities in a simple one-pot procedure under mild conditions.

A novel one-pot synthesis of secondary alcohols from esters

Alkylation or vinylation by using organometallic reagents after partial reduction of carboxylic esters with LDBBA gave secondary alcohols, also involving allyl alcohols, without any isolation of intermediates in good yield (54-78%).

Empirical method for predicting enantioselectivity in catalytic reactions: demonstration with lipase and oxazaborolidine

We derived a novel equation capable of predicting the degree of enantioselectivity in a catalytic reaction without any knowledge of the reaction mechanism and/or the transition-state structure, and tested the validity of this equation by changing substrates systematically in the lipase or oxazaborolidine-catalyzed reactions. A good correlation was observed between the predicted and observed E values, and the stereochemistry of the products could be predicted correctly in most cases (28 out of 30).

Construction of cyclopentyl carbinols from ω-tosyloxy-1-alkenyl boronate esters and grignard reagents

Addition of RMgCl (R = n-Bu, Ph) to pinacol esters of 6-tosyloxy-l-alkenyl boronic acids at -78 °C gave the borates, which upon warming to room temperature underwent migration of R on boron to C(1) carbon and concomitant ring construction C-C bond formati

Highly enantioselective 1,2-additions of various organolithium reagents to aldehydes

Several asymmetric 1,2-additions of various organolithium reagents (methyllithium, n-butyllithium, phenyllithium, lithioacetonitrile, lithium n-propylacetylide, lithium phenylacetylide) to aldehydes are shown to result in decent to excellent enantiomeric excesses (65-98%) when performed in the presence of a chiral lithium amido sulfide. The chiral lithium amido sulfides invariably exhibited higher levels of enantioselectivity in all the reactions tested, compared to the structurally similar chiral lithium amido ethers and the chiral lithium amide without a chelating group.

Chlorodimethylaluminum-promoted nucleophilic addition of lithium pentamethylcyclopentadienide to aliphatic aldehydes and DDQ-mediated carbon-carbon bond cleavage of the adducts providing the parent aldehydes

Treatment of aliphatic aldehyde with lithium pentamethylcyclopentadienide in the presence of chlorodimethylaluminum provided the corresponding carbinol in excellent yield. The carbinol returns to the parent aldehyde and pentamethylcyclopentadiene by the a

Pentamethylcyclopentadienide in organic synthesis: Nucleophilic addition of lithium pentamethylcyclopentadienide to carbonyl compounds and carbon-carbon bond cleavage of the adducts yielding the parent carbonyl compounds

Lithium pentamethylcyclopentadienide (C5Me5Li, Cp*Li) reacted with aromatic aldehyde to provide the corresponding carbinol in excellent yield. The carbinol returns to the parent aldehyde and pentamethylcyclopentadiene upon exposure to acid or due to heating. Chlorodimethylaluminum is essential as an additive to attain the nucleophilic addition of Cp*Li to aliphatic aldehyde. The carbinol derived from aliphatic aldehyde returns to the parent aldehyde and pentamethylcyclopentadiene by the action of a catalytic amount of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ). The reversible addition/elimination of the Cp* group can represent a protection of aldehyde. Mechanistic details of the carbon-carbon bond cleavage are also disclosed.

Nickel-catalyzed alkylation of aldehydes with trialkylboranes

(Chemical Equation Presented) Nickel-catalyzed alkylation of aldehydes with trialkylboranes proceeds smoothly in the presence of a catalytic amount of 5-allyl-1,2,3,4,5-pentamethyl-1,3-cyclopentadiene or an excess of cesium carbonate to afford the corresponding secondary alcohols.