75851-76-2

Upstream product

• 4784-77-4 (E/Z)-crotyl bromide 
• 100-52-7 benzaldehyde 
• 504-61-0 (E)-but-2-enol 
• 22032-77-5 (E)-crotylmagnesium chloride 
• 31197-41-8 crotyltributylstannane 
• 35998-93-7 tri-n-butylcrotyltin 
• 563-52-0 2-chloro-3-butene 
• 95-14-7 1,2,3-Benzotriazole 
• 4784-77-4 (E)-1-Bromo-2-butene 
• 19781-52-3 2,3-dimethylpent-4-en-2-ol 
• 74087-85-7 3,3-dimethyldioxirane 
• 1588-56-3 trans-2-phenyl-1-ethylcyclopropane 
• 18292-28-9 1-(trimethylsilyl)but-2-ene 
• 4894-61-5 trans-but-2-enyl chloride 

Downstream Products

• 583-03-9 1-Phenyl-1-pentanol 
• 73481-93-3 1-phenylpent-3-en-1-one 
• 304459-85-6 4-methyl-1-phenyl-hex-5-en-3-ol 
• 169827-07-0 (E)-1-phenyl-hept-5-en-3-ol 

Relevant academic research and scientific papers

ALLYLSTANNATION. II. A TOTAL "cis-PREFERENCE" IN THE ADDITION OF n-Bu2ClSnCH(CH3)CH=CH2 TO ALDEHYDES

1-Buten-3-yldi-n-butylchlorotin, formed by redistribution of (E/Z)-2-butenyltri-n-butyltin and Bu2SnCl2, reacts readily with neat RCHO (R = C2H5, C2H5(CH3)CH, (CH3)2CH, (CH3)3C and C6H5) to give high yields (80-100percent) of alcohols of the type RCH(OH)C

Bismuth mediated barbier synthesis of α-homoallylic alcohols via a sigmatropic rearrangement in [bmim][HSO4]

A novel protocol for the Bismuth metal mediated regioselctive crotylation of aldehydes yielding α-homoallylic alcohols has been developed using 20mol% [bmim][HSO4] as a metal activator, as well as a mediator for regioconversion from the initially formed γ-regiomer. The present protocol minimizes the use of conventional solvents and proceeds with good yields and excellent regioselectivities.

Nickel-catalyzed remote hydrosilylation of unconjugated enones with bulky triphenylsilane

Herein we describe a nickel-catalyzed remote hydrosilylation of unconjugated enones with bulky triphenylsilane. A range ofZ-silyl enol ethers are obtained as major isomers due to the process of nickel triggered alkene isomerization. Notably, some specific

Palladium-catalyzed double-bond migration of unsaturated hydrocarbons accelerated by tantalum chloride

The operationally simple palladium-catalyzed double-bond migration without heteroatom-containing coordinating functional groups is described. Addition of TaCl5 as a second catalyst greatly enhanced the migration efficiency to provide β-alkylsty

Indium-mediated allylation of carbonyl compounds in ionic liquids: Effect of salts in ionic liquids

The In-mediated allylation of carbonyl compounds can be performed in various types of solvents including ionic liquids. However, we have found that in [bmim][BF4] (where bmim = 1-butyl-3-methylimidazolium), the In-mediated coupling of crotyl bromide with benzaldehyde gives a complex mixture, and some additives, such as halides and amines, are crucial for the successful conversion to the corresponding γ-adduct. Instead, the addition of alcohols or water promotes the formation of the α-adduct. An asymmetric induction with up to 62% enantiomeric excess (ee) was observed employing cinchonidine as an additive in a binary solvent consisting of an ionic liquid and dichloromethane.

Hot water-promoted cyclopropylcarbinyl rearrangement facilitates construction of homoallylic alcohols

In refluxing 9 : 1 (v/v) H2O-1,4-dioxane and without an additional catalyst, the rearrangements of various types of cyclopropyl carbinols were attempted. It was found that the reactions generally gave homoallylic alcohols in good to very high chemical yields. Rearrangements of bicyclic or tricyclic cyclopropyl carbinols readily gave the desired ring-expanded cyclic homoallylic alcohols which are difficult to synthesize by other means.

Prins cyclization of α-bromoethers under basic conditions

α-Bromoethers have been found to undergo Prins-type cyclization under basic conditions and without the need to add a promoter. The products are those derived from a Markovnikov addition on the pendant alkene. However, the stereochemistry and even the structure of the products sometimes differ from those expected with the classical Lewis-acid-catalyzed Prins reaction of acetals.

Highly stereoselective synthesis of z-homoallylic alcohols by kinetic resolution of racemic secondary allyl boronates

α to Z: Racemic α-chiral allyl boronates, which are readily synthesized from the respective primary allyl halides, undergo a highly efficient kinetic resolution in a face- and Z-selective allylation of aldehydes catalyzed by the chiral Bronsted acid (R)-TRIP (see scheme; Epin=tetraethylethylene glycol). Copyright

Allylation reactions of aldehydes with allylboronates in aqueous media: Unique reactivity and selectivity that are only observed in the presence of water

Zn(OH)2-catalyzed allylation reactions of aldehydes with allylboronates in aqueous media have been developed. In contrast to conventional allylboration reactions of aldehydes in organic solvents, the α-addition products were obtained exclusively. A catalytic cycle in which the allylzinc species was generated through a B-to-Zn exchange process is proposed and kinetic studies were performed. The key intermediate, an allylzinc species, was detected by HRMS (ESI) analysis and by online continuous MS (ESI) analysis. This analysis revealed that, in aqueous media, the allylzinc species competitively reacted with the aldehydes and water. An investigation of the reactivity and selectivity of the allylzinc species by using several typical allylboronates (6a, 6b, 6c, 6d) clarified several important roles of water in this allylation reaction. The allylation reactions of aldehydes with allylboronic acid 2,2-dimethyl-1,3-propanediol esters proceeded smoothly in the presence of catalytic amounts of Zn(OH)2 and achiral ligand 4d in aqueous media to afford the corresponding syn-adducts in high yields with high diastereoselectivities. In all cases, the α-addition products were obtained and a wide substrate scope was tolerated. Furthermore, this reaction was applied to asymmetric catalysis by using chiral ligand 9. Based on the X-ray structure of the Zn-9 complex, several nonsymmetrical chiral ligands were also found to be effective. This reaction was further applied to catalytic asymmetric alkylallylation, chloroallylation, and alkoxyallylation processes and the synthetic utility of these reactions has been demonstrated. Still waters run deep: The Zn(OH)2-catalyzed allylation of aldehydes with allylboronates in aqueous media exclusively afford the α-addition products. This reaction was also applied to alkylallylation, chloroallylation, and alkoxyallylation reactions. The role of water is discussed. Copyright

Cobalt-salen complex-catalyzed oxidative generation of alkyl radicals from aldehydes for the preparation of hydroperoxides

Catalytic generation of alkyl radicals from aldehydes via oxidative deformylation was realized using a cobalt-salen complex with H2O 2. The deformylation was thought to proceed through homolytic cleavage of peroxohemiacetal intermediates to provide even primary alkyl radicals under mild conditions. Variously substituted and functionalized hydroperoxides were obtained from corresponding aldehydes in good yield.