111957-98-3

Upstream product

• 75-07-0 acetaldehyde 
• 106-95-6 allyl bromide 
• 1730-25-2 allylmagnesium bromide 
• 930-22-3 epoxybutene 
• 917-54-4 methyllithium 
• 2833-31-0 acetic acid 1-methylbut-3-enyl ester 
• 591-93-5 1,4-Pentadiene 
• 534-15-6 1,1-dimethoxyethane 
• 64549-05-9 allyldibutyltin chloride 
• 598-18-5 2-bromopropanol 
• 3536-96-7 vinylmagnesium chloride 
• 130436-12-3 C₁₁H₁₃NO₃S 
• 556-56-9 allyl iodid 
• 2622-05-1 allylmagnesium bromide 

Downstream Products

• 64584-91-4 phthalic acid mono-(1-methyl-but-3-enyl) ester 
• 64584-92-5 (R)-pent-4-en-2-ol 
• 625-67-2 2,4-dichloropentane 
• 10524-08-0 4-Chlor-pent-1-en 
• 31950-56-8 4-bromopent-1-ene 
• 107-87-9 2-Pentanone 
• 117174-90-0 4-(N-(benzyloxycarbonyl)aminomethoxy)-1-pentene 
• 150042-95-8 C₁₅H₂₆OSi₂ 
• 150042-96-9 C₂₅H₃₀OSi₂ 
• 40844-09-5 ((pent-4-en-2-yloxy)methyl)benzene 
• 99483-17-7 pent-4-en-2-yl benzoate 
• 52753-86-3 pent-4-en-2-yl 4-methylbenzenesulfonate 
• 1569-50-2 3-penten-2-ol 
• 71-41-0 pentan-1-ol 

Relevant academic research and scientific papers

Sila-Substituted Perfumes and Isosteric Compounds of Perfumes. X. A Novel Route to Sila-β-Ionone

Preparation of sila-β-ionone (14) was possible by a novel route with yields nearly 5 times higher than before, with the formerly unknown 1,1,3-trimethyl-1-silacyclohexanone-2 (6) as a key substance.The nine reaction steps may be seen from Scheme 1. 2-Ethinyl-1,1,3-trimethyl-1-silacyclohexan-2-ol (7) could not be dehydrated to give the analogous silacyclohexene derivative 9.But dehydration was successful in the case of 2-(1-butin-3-ol) substituents; here only the ring but not the chain hydroxyl group was eliminated. - Keywords: Sila-perfumes; Silacyclohexanon-2; Sila-β-ionone

A simple and efficient approach to 1,3-polyols: Application to the synthesis of cryptocarya diacetate

A highly enantio- and stereoselective synthetic strategy for both syn-and anti-1,3-polyols has been developed. The sequence involves iterative Jacobsen's hydrolytic kinetic resolution (HKR), diastereoselective iodine-induced electrophilic cyclization, and ring-closing metathesis (RCM). This protocol has subsequently been utilized for the synthesis of cryptocarya diacetate, a natural product with broad range of biological activity.

Synthetic Studies toward the C32-C46 Segment of Hemicalide. Assignment of the Relative Configuration of the C36-C42 Subunit

The synthesis of five diastereomeric model compounds incorporating the C32-C46 segment of the antitumor marine natural product hemicalide has been achieved through a convergent approach relying on the 1,4-addition of an alkenyl boronate to an α,β-unsaturated δ-lactone followed by α-hydroxylation of an enolate and a Julia-Kocienski olefination. Comparison of the 1H and 13C NMR data of the model compounds with those of hemicalide enabled the assignment of the relative configuration of the C36-C42 subunit. (Chemical Equation Presented).

Barbier-type carbonyl-allylation with allyl compounds and SnCl2 in the presence of PdCl2[PPh2(m-C6H4SO 3Na)]2 under two-phase conditions

The hydrophilic palladium complex efficiently catalyzes the allylation of carbonyl compounds with allyl chlorides or allyl alcohols and SnCl2 under aqueous-organic biphase conditions, which allow us easily to separate the product and to recover the organic solvent from the reaction mixture.

Stereoselective synthesis of (+)-cryptocarya diacetate by an iterative Prins cyclisation and reductive cleavage sequence

A highly stereoselective synthesis of (+)-cryptocarya diacetate is achieved through our recently developed strategy for the construction of 1,3-diols via Prins cyclisation. The route relies mainly on the reductive cleavage of allylic ethers, ozonolysis and Wittig olefination along with Prins cyclisation.

Synthesis and Stereochemical Assignment of Arenolide

The convergent synthesis of candidate stereoisomers of the natural product arenolide was accomplished using recently developed catalytic boron-based reactions. Comparison of the spectral data for candidate structures with that reported for the authentic natural product revealed the likely stereostructure of the natural compound.

Total synthesis of (–)-cephalosporolide D

In this communication, a concise and efficient synthetic route for the synthesis of (–)-Cephalosporolide D in enantioselective way has been described. In this synthesis, Mitsunobu esterification and Ring Closing Metathesis (RCM) for macrocyclic ring formation have been applied as key steps.

Copper-Catalyzed Enantiotopic-Group-Selective Allylation of gem-Diborylalkanes

We report a copper-catalyzed enatiotopic-group-selective allylation of gem-diborylalkanes with allyl bromides. The combination of copper(I) bromide and H8-BINOL derived phosphoramidite ligand proved to be the most effective catalytic system to provide various enantioenriched homoallylic boronate esters, containing a boron-substituted stereogenic center that is solely derived from gem-diborylalkanes, in good yields with high enantiomeric ratios under mild conditions. Experimental and theoretical studies have been conducted to elucidate the reaction mechanism, revealing how the enatiotopic-group-selective transmetalation of gem-diborylalkanes with chiral copper complex occurs to generate chiral α-borylalkyl-copper species for the first time. Additional synthetic applications to the synthesis of various chiral building blocks are also included.

Dialkyl Ether Formation at High-Valent Nickel

In this article, we investigated the I2-promoted cyclic dialkyl ether formation from 6-membered oxanickelacycles originally reported by Hillhouse. A detailed mechanistic investigation based on spectroscopic and crystallographic analysis revealed that a putative reductive elimination to forge C(sp3)-OC(sp3) using I2 might not be operative. We isolated a paramagnetic bimetallic NiIII intermediate featuring a unique Ni2(OR)2 (OR = alkoxide) diamond-like core complemented by a μ-iodo bridge between the two Ni centers, which remains stable at low temperatures, thus permitting its characterization by NMR, EPR, X-ray, and HRMS. At higher temperatures (>-10 °C), such bimetallic intermediate thermally decomposes to afford large amounts of elimination products together with iodoalkanols. Observation of the latter suggests that a C(sp3)-I bond reductive elimination occurs preferentially to any other challenging C-O bond reductive elimination. Formation of cyclized THF rings is then believed to occur through cyclization of an alcohol/alkoxide to the recently forged C(sp3)-I bond. The results of this article indicate that the use of F+ oxidants permits the challenging C(sp3)-OC(sp3) bond formation at a high-valent nickel center to proceed in good yields while minimizing deleterious elimination reactions. Preliminary investigations suggest the involvement of a high-valent bimetallic NiIII intermediate which rapidly extrudes the C-O bond product at remarkably low temperatures. The new set of conditions permitted the elusive synthesis of diethyl ether through reductive elimination, a remarkable feature currently beyond the scope of Ni.

A Short Synthesis of (+)-Brefeldin C through Enantioselective Radical Hydroalkynylation

A very concise total synthesis of (+)-brefeldin C starting from 2-furanylcyclopentene is described. This approach is based on an unprecedented enantioselective radical hydroalkynylation process to introduce the two cyclopentane stereocenters in a single step. The use of a furan substituent allows a high trans diastereoselectivity to be achieved during the radical process and it contains the four carbon atoms C1–C4 of the natural product in an oxidation state closely related to the one of the target molecule. The eight-step synthesis requires six product purifications and it provides (+)-brefeldin C in 18 % overall yield.