104683-47-8

Upstream product

• 140439-75-4 (Z)-4-hydroxybut-2-en-1-yl methyl carbonate 
• 100-52-7 benzaldehyde 
• 930-22-3 epoxybutene 
• 6117-80-2 1,4-butenediol 
• 143446-91-7 cis-5-phenyl-2-phenyl-4-vinyl-1,2-oxaborolane 

Relevant academic research and scientific papers

Diastereoselective Reactions of δ-Siloxyallylzirconium Reagents with Aldehydes

δ-Siloxyallylzirconium reagent (2) was produced by reaction of the TBDMS protected derivative (6) with zirconocene butene complex "Cp2Zr".Treatment of the δ-siloxyallylzirconium reagent (2) with various aldehydes provided predominantly anti-homoallylic alcohols.

Enantioselective anti- And syn-(borylmethyl)allylation of aldehydes via br?nsted acid catalysis

The enantioselective anti- and syn-(borylmethyl)allylation of aldehydes via phosphoric acid catalysis is reported. Both (E)- and (Z)-γ-borylmethyl allylboronate reagents were prepared via the Cu-catalyzed highly stereoselective protoboration of 1,3-dienyl

Nickel-catalyzed borylative ring opening of vinyl epoxides and aziridines

Image Presented A mild ring opening of vinyl epoxides and aziridines with B2Pin2 catalyzed by Ni(0)-Binap affords new functionalized allylic boron derivatives which undergo sequential transformations. The uncatalyzed allylation of al

Reaction of 1-Phenyl-3-borolenes with Aldehydes, Ketones, and Ketenes: Synthesis of 1,2-Oxaborolane Derivatives, 2,3-anti-1,3-Diols and Unsaturated β-Hydroxyalkyl Ketones

1-Phenyl-3-borolenes (1a: R1 = H; b R1 = Me) react with aldehydes R2CHO to give cis-1,2-oxaborolanes (2, R2 = e.g.Me, Ph, CH=CH2, tBu, CCl3, R3 = H).Yields are nearly quantitative.Stereoselectivities usually are 100percent (but only 95percent for R2 = CH=CH2, 97percent for R2 = Me).Oxidation with NaOH/H2O2 in THF affords homoallylic anti-1,3-diols HOCR2R3-CR11(=CH2)>CH2OH (3).An X-ray diffraction analysis of 3a (R2 = p-tolyl) proves the assigned stereochemistries.Ketones R2R3CO react analogously.Ketenes R2CCO form 5-alkylidene-4-vinyl-1,2-oxaborolanes (4), which tend to undergo double-bond migration.Oxidation produces two types of β-hydroxyalkyl ketones R22CHCOCCH2OH (5) and R22CHCOCMeCH2OH (6).Key Words: Diastereoselective synthesis / Homoallylic alcohols / 1,3-Diols, homoallylic / β-Hydroxyalkyl ketones / 2,5-Dihydro-1H-boroles / 1,2-Oxaborolanes

Palladium-catalyzed carbonyl allylation by allylic alcohols with SnCl2

Allylic alcohols can be applied to carbonyl allylation via the formation of π-allylpalladium complexes, using palladium as catalyst and SnCl2 as a reducing agent. This reaction has chemoselectivity: The reactivity order of allylating agents is allylic carbonate > allylic alcohol > allylic acetate, and that of carbonyl compounds is aldehyde > ketone. High regioselcction was observed in polar solvents such as DMF, DMI, and DMSO; carbonyl compounds apparently attacked the more substituted allylic position of π-allylpalladium complexes to afford only one regioisomer. Diastereocontrol in the carbonyl allylation of aromatic aldehydes by (E)-2-butenol was achieved by the choice of polar solvents; use of DMSO at 25 °C led to syn selection, while anti selection was found at -10 °C in THF. The addition of H2O in any solvent accelerated the carbonyl allylation and enhanced both regioselectivity and the diastereoselectivity. Anti selection in DMF, DMI, and THF-H2O can be explained by the chair form of the six-membered cyclic transition state, while syn selection in DMSO allows us to propose an acyclic antiperiplanar transition state. An NMR spectroscope investigation demonstrated that the actual allylating agent in dry medium was allyltrichlorotin: 1H, 13C, and 119Sn NMR spectra of the reaction of allyl alcohol with PdCl2(PhCN)2-SnCl2 in DMF-d7. corresponded to those of the reaction of allyl chloride with PdCl2(PhCN)2-SnCl2 in DMF-d7.

Palladium-catalyzed carbonyl allylation by 2-(hydroxymethyl)acrylate derivatives: Synthesis of α-methylene-γ-butyrolactones

Ethyl 2-(hydroxymethyl)acrylate derivatives serve as reagents for 2-ethoxycarnonylallylation of carbonyl compounds using PdCl2(PhCN)2-SnCl2 system to produce α-methylene-γ-butyrolactones diastereoselectively.