109062-28-4

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 106-99-0 buta-1,3-diene 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 79705-05-8 (E)-1-(prop-2-yn-1-yloxy)but-2-ene 
• 79705-07-0 (3S,4R)-4-Methyl-hex-5-en-1-yn-3-ol 
• 1357478-15-9 (±)-2-(but-3-en-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 69611-01-4 (Z)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 591-50-4 iodobenzene 
• 88088-48-6 (3S,4R)-4-Methyl-1-trimethylsilanyl-hex-5-en-1-yn-3-ol 
• 88088-42-0 {3-[((E)-But-2-enyl)oxy]-prop-1-ynyl}-trimethyl-silane 
• 35998-93-7 tri-n-butylcrotyltin 
• 31197-41-8 crotyltributylstannane 
• 18147-55-2 (Z)-crotyltrichlorosilane 
• 18147-55-2 but-2-enyltrichlorosilane 

Downstream Products

• 88155-83-3 methyl (E)-(3R^*,4S^*)-4-methoxy-3-methyl-6-phenylhexa-5-enoate 
• 88088-56-6 (E)-(3R,4S)-4-Methoxy-3-methyl-6-phenyl-hex-5-enoic acid 
• 88088-55-5 (E)-(3S,4S)-4-Methoxy-3-methyl-6-phenyl-hex-5-en-1-ol 
• 88088-55-5 (E)-(3R^*,4S^*)-4-methoxy-3-methyl-6-phenylhex-5-enol 
• 88088-54-4 (E)-(3S^*,4R^*)-3-methoxy-4-methyl-1-phenylhexa-1,5-diene 

Relevant academic research and scientific papers

Carbonyl allylations by allylic chlorides utilizing a reduction of tin(IV) iodide to triiodostannate(II) species with iodide sources

Carbonyl allylations by allylic chlorides either with tin(IV) iodide and tetrabutylammonium iodide (TBAI) in dichloromethane or with tin(IV) iodide and sodium iodide in 1,3-dimethylimidazolidin-2-one at room temperature produced the corresponding homoallylic alcohols. The carbonyl allylations probably proceeded via the reduction of tin(IV) iodide to triiodostannate(II) species with iodide sources such as TBAI and NaI, which led to the construction of a tin(IV)-catalytic cycle based on regeneration of tin(IV) iodide via the transmetalation of homoallyloxytriiodotin to homoallyloxytrimethylsilane with iodotrimethylsilane.

Metal free synthesis of homoallylic alcohols promoted by ultrasound

The use of ultrasound irradiation to promote the allylation of aldehydes containing different functionalities with potassium allyltrifluoroborates is described. The method features the use of a minimum amount of acetone as solvent, without any other catalyst or promoter. The products were obtained in high yields, short reaction times, at room temperature and without the need of further purification.

Catalytic organic reactions on the surface of silver(I) oxide in water

We have developed Ag2O-catalyzed allylation reactions of aldehydes with allylsilanes in water, providing homoallylic alcohols in high yields with high anti-selectivities. It was found that the reactions proceeded not in the water solution but o

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

COMPOSITIONS AND METHODS FOR STEREOSELECTIVE ALDEHYDE ALLYLATION AND CROTYLATION

Compositions and methods for practical, stereoselective allylation and crotylation for aldehyde substrates are described. The compositions and methods comprise reagents for allylation and/or crotylation and acids. In some embodiments, the reagents and acids are pre-mixed.

A more comprehensive and highly practical solution to enantioselective aldehyde crotylation

The enantioselective crotylation of aldehydes with 1,2- diaminochlorocrotylsilane reagents is effectively catalyzed by Sc(OTf) 3. The one significant limitation on the utility of these reagents-substrate scope-has thus been addressed. The net r

Iridium-catalyzed hydrohydroxyalkylation of butadiene: Carbonyl crotylation

Exposure of alcohols 1a-1i to butadiene in the presence of a cyclometallated iridium catalyst derived from allyl acetate, 4-methoxy-3-nitrobenzoic acid and 2,2′-bis(diphenylphosphino)biphenyl (BIPHEP) results in hydrogen transfer to generate aldehyde-allyliridium pairs, which engage in C-C coupling to form products of carbonyl crotylation. Under related conditions using 1,4-butanediol as hydrogen donor, butadiene reductively couples to aldehydes 2e-2g and 2i to furnish carbonyl crotylation products 3e-3g and 3i. Thus, butadiene-mediated carbonyl crotylation occurs with equal facility from the alcohol or aldehyde oxidation level with complete levels of branched regioselectivity.

Allylation of aldehydes promoted by the cerium(III) chloride heptahydrate/sodium iodide system: The dependence of regio- and stereocontrol on the reaction conditions

The cerium(III) chloride heptahydrate/sodium iodide complex (CeCl 3·7 H2O/NaI) acts as a useful promoter in the carbon-carbon bond forming reaction by addition of allyltributylstannanes to aldehydes. The reaction of 2-butenyltributyl

Gallium-mediated allyl transfer from bulky homoallylic alcohol to aldehydes via retro-allylation: Stereoselective synthesis of both erythro- and threo-homoallylic alcohols

(Chemical Equation Presented) Retro-allylation of bulky gallium homoallylic alkoxides occurs to generate (Z)- and (E)-crotylgallium reagents stereospecifically, starting from erythro- and threo-homoallylic alcohols, respectively. The (Z)- and (E)-crotylgallium reagents immediately reacted with aromatic aldehydes to afford the corresponding erythro and threo-homoallylic alcohols, respectively.

A Mild Protocol for Allylation and Highly Diastereoselective Syn or Anti Crotylation of Aldehydes in Biphasic and Aqueous Media Utilizing Potassium Allyl- and Crotyltrifluoroborates

(Equation Presented) Potassium allyl- and crotyltrifluoroborates undergo addition to aldehydes in biphasic media as well as water to provide the corresponding homoallylic alcohols in high yields (≥94%), excellent diastereoselectivity (dr ≥ 98:2), and with