130930-52-8

Upstream product

• 123-73-9 trans-Crotonaldehyde 
• 931-50-0 cyclohexylmagnesium bromide 
• 542-18-7 cyclohexyl chloride 
• 114180-68-6 α-cyclohexyl-3-methyloxiranemethanol 
• 123-73-9 crotonaldehyde 
• 126403-69-8 (Z)-1-Propenylzinc bromide 
• 2043-61-0 cyclohexanecarbaldehyde 
• 590-13-6 (Z)-1-propenyl bromide 
• 132350-99-3 lithium N-methylephedrate 
• 79646-42-7 (E)-1-cyclohexyl-2-buten-1-ol 
• 126403-69-8 (E)-prop-1-enylzinc(II) bromide 
• 590-15-8 trans-2-propenyl bromide 
• 15378-40-2 trans-1-cyclohexyl-2-buten-1-one 
• 18736-82-8 1-cyclohexyl-but-2-en-1-ol 

Downstream Products

• 163181-69-9 1-Acetoxy-1-cyclohexyl-2-butene 
• 79646-42-7 (2E,1R)-1-cyclohexyl-2-buten-1-ol 
• 18736-82-8 (2E,1S)-1-cyclohexyl-2-buten-1-ol 
• 114180-65-3 (S)-Cyclohexyl-((2S,3S)-3-methyl-oxiranyl)-methanol 
• 79605-71-3 (S)-Cyclohexyl-((2R,3R)-3-methyl-oxiranyl)-methanol 
• 15378-40-2 trans-1-cyclohexyl-2-buten-1-one 
• 114180-68-6 α-cyclohexyl-3-methyloxiranemethanol 
• 109177-13-1 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (E)-1-cyclohexyl-but-2-enyl ester 
• 114180-63-1 (E)-2-(4-cyclohexylbut-3-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 54130-58-4 3-Methyl-5-cyclohexyl-trans-4-pentensaeure-aethylester 
• 335627-62-8 ((E)-1-Chloro-but-2-enyl)-cyclohexane 
• 1059574-48-9 (E)-o-diphenylphosphanylbenzoic acid 1-cyclohexylbut-2-enyl ester 
• 1613417-30-3 (S)-(E)-tert-butyl 6-(4-cyclohexyl-2-((methylcarbamoyl)thio)but-3-en-2-yl)-1H-indole-1-carboxylate 
• 1613416-91-3 (S)-(E)-4-cyclohexyl-2-(3-methoxyphenyl)but-3-ene-2-thiol 

Relevant academic research and scientific papers

Multi-gram-scale synthesis of a versatile syn-anti stereotriad by a short and cost-effective route

The polyketide family of natural products includes numerous biologically important molecules that exhibit a variety of complex structures. The biosynthesis of these diverse structures relies on the iterative assembly of individual segments controlled by t

Tuning of α-Silyl Carbocation Reactivity into Enone Transposition: Application to the Synthesis of Peribysin D, E-Volkendousin, and E-Guggulsterone

A reliable method for enone transposition has been developed with the help of silyl group masking. Enantio-switching, substituent shuffling, and Z-selectivity are the highlights of the method. The developed method was applied for the first total synthesis of peribysin D along with its structural revision. Formal synthesis of E-guggulsterone and E-volkendousin was also claimed using a short sequence.

Copper Hydride Catalyzed Reductive Claisen Rearrangements

An efficient reductive Claisen rearrangement, catalyzed by in situ generated copper hydride and stoichiometric in diethoxymethylsilane, has been developed. Yields of up to 95 ;% with good to excellent diastereoselectivities were observed in this reaction. Mechanistic studies showed that the stereospecific rearrangement proceeded via a chair transition state of (E)-silyl ketene acetals as intermediates and not via the copper enolates.

Chirality Transfer in Gold(I)-Catalysed Direct Allylic Etherifications of Unactivated Alcohols: Experimental and Computational Study

Gold(I)-catalysed direct allylic etherifications have been successfully carried out with chirality transfer to yield enantioenriched, γ-substituted secondary allylic ethers. Our investigations include a full substrate-scope screen to ascertain substituent effects on the regioselectivity, stereoselectivity and efficiency of chirality transfer, as well as control experiments to elucidate the mechanistic subtleties of the chirality-transfer process. Crucially, addition of molecular sieves was found to be necessary to ensure efficient and general chirality transfer. Computational studies suggest that the efficiency of chirality transfer is linked to the aggregation of the alcohol nucleophile around the reactive π-bound Au-allylic ether complex. With a single alcohol nucleophile, a high degree of chirality transfer is predicted. However, if three alcohols are present, alternative proton transfer chain mechanisms that Erode the efficiency of chirality transfer become competitive.

Dihydrothiophenes containing quaternary stereogenic centres by sequential stereospecific rearrangements and ring-closing metathesis

Stereospecific [3,3]-sigmatropic rearrangement of O-substituted thiocarbamate derivatives of enantiopure allylic alcohols provides allylic thiocarbamates as single enantiomers. Intramolecular arylation by rearrangement of their allyllithium derivatives provides allylic tertiary thiols. Allylation and ring-closing metathesis gives 2,5-dihydrothiophenes containing sulfur-bearing quaternary centres. This journal is the Partner Organisations 2014.

Highly stereoselective C-C bond formation by rhodium-catalyzed tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor carbenoids and chiral allylic alcohols

The tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor rhodium carbenoids and chiral allyl alcohols is a convergent C-C bond forming process, which generates two vicinal stereogenic centers. Any of the four possible stereoisomers can be selectively synthesized by appropriate combination of the chiral catalyst Rh2(DOSP)4 and the chiral alcohol.

Asymmetric catalysis route to anti,anti stereotriads, illustrated by applications

(Chemical Equation Presented) A short sequence based on asymmetric catalysis, chirality transfer, and an optimized carbometallation protocol gave an anti,anti stereotriad building block in six steps. Both enantiomers of the chirality source, N-methyl ephedrine, are inexpensive, and the auxiliary is recoverable. In one chiral series, the building block was converted to the B-2 intermediate in Miyashita's synthesis of scytophycin C; in the enantiomeric series, it was converted to a key intermediate for aplyronine A and to the polyketide cap for the callipeltins.

Intermediates for the synthesis of polypropionate antibiotics

The invention relates to intermediate compounds of the formula wherein R1 is H or a protecting group, R2 and R3 each independently represent H, methyl, or a leaving group, provided that at least one, but not both, of Rsup

Stereospecific reaction of α-carbamoyloxy-2-alkenylboronates and α-carbamoyloxy-alkylboronates with grignard reagents - Synthesis of highly enantioenriched secondary alcohols

Highly enantioenriched secondary alcohols were synthesized by treatment of α-carbamoyloxy-2-alkenylboronates and α-carbamoyloxy-alkylboronates with Grignard reagents. An intermediary boronate complex was transformed stereospecifically to the corresponding secondary 2-alkenyl- and alkylboronates by migration of an introduced residue. Oxidative workup furnished the enantioenriched secondary alcohols.

Stereoselective reactions of acyclic allylic phosphates with organocopper reagents

A series of acyclic allylic alcohols of general structure R1CH=CHCH(OH)R2 were resolved by Sharpless kinetic resolution. The hydroxyl groups of these enantiomerically enriched alcohols were derivatized to diethyl phosphates, and the derivatives were reacted with organocopper reagents. Cleanest substitution reactions were observed with reagents R32CuCNLi2. With R1 = Me and R3 = n-Bu, the size of R2 affected both the regioselectivity and stereoselectivity of the displacement. Larger R2 groups gave higher regio- and stereoselectivities: with R2 = 3-pentyl, >98% SN2′ regioselectivity and > 98% anti stereoselectivity were observed. Bn2CuCNLi2 gave stereoselectivities comparable to those observed with n-Bu2CuCNLi2 but t-Bu2CuCNLi2 exhibited much lower diastereofacial preference.