62499-97-2

Upstream product

• 100-51-6 benzyl alcohol 
• 52547-82-7 1-hydroxy-1-phenyl-4-(tetrahydropyran-2'-yloxy)but-2-yne 
• 100-52-7 benzaldehyde 
• 107-19-7 propargyl alcohol 

Downstream Products

• 124244-39-9 2-phenyl-2,5-dihydrofuran 
• 55177-35-0 4-phenylbut-2-enal 
• 17113-33-6 2-phenylfuran 
• 96227-91-7 (RS,E)-2,2-dimethyl-4-styryl-1,3-dioxolane 
• 96227-95-1 2,2-Dimethyl-4-phenyl-4,7-dihydro-[1,3]dioxepine 
• 4850-50-4 1-phenyl-butane-1,4-diol 
• 16133-83-8 tetrahydro-2-phenylfuran 
• 1040285-21-9 (E)-4-(2-phenylvinyl)-2-(trichloromethyl)-4,5-dihydro-1,3-oxazole 
• 1307905-23-2 methyl (E)-2-[(tert-butoxycarbonyl)amino]-4-phenylbut-3-enoate 
• 132803-75-9 (+/-)-(3E)-2-amino-4-phenylbut-3-en-1-ol 
• 312521-54-3 (E)-2-t-butoxycarbonylamido-4-phenyl-3-butene-1-ol 
• 1307904-92-2 2,2,2-trichloroacetimidic acid (Z)-1-phenyl-4-(2,2,2-trichloroacetimidoyloxy)but-2-enyl ester 

Relevant academic research and scientific papers

Ni(0)-catalyzed 1,4-selective diboration of conjugated dienes

Figure Presented. A catalytic stereoselective 1,4-diboration of conjugated dienes with B2(pin)2 was accomplished with Ni(cod) 2 and PCy3 as the catalyst. This reaction broadens the substrate scope of current methods for catalytic diene diboration by including internal and sterically hindered dienes, and it proceeds efficiently at low catalyst loadings. The intermediate allylboronate was oxidized to the stereodefined allylic 1,4-diol.

Conversion of (Z)-1,4-dihydroxyalk-2-enes into 2,5-dihydrofurans and of alkane-1,4-diols into tetrahydrofurans via acid-catalysed cyclisation of the monoisoureas formed by their copper(I)-mediated reactions with dicyclohexylcarbodiimide

(Z)-1,4-dihydroxyalk-2-enes were converted into 2,5-dihydrofurans and alkane-1,4-diols were converted into tetrahydrofurans via acid-catalysed cyclisation of the monoisoureas. The reaction involved protonation of the carbodiimide by acidic phenol followed by reaction with alkanol. Pd/CaCo3-quinoline catalyst system was employed in the presence of a little triethylamine to overcome partial hydrogenolysis.

Doubly Metalated Methanol. - Alcohol d1- and d3-Reagents

The nucleophilic counterpart of the electrophilic hydroxymethylating protonated formaldehyde B is the hypothetical tautomer A, R = H, of methoxide.Experiments are described in which the generation of doubly metalated methanol C (= formaldehyde ketyl dianion) and its use as methanol d1-reagent are attempted.Treatment of stannylated methanol 1 with two equivalents of butyllithium furnishes a pentane-soluble reagent which hydroxymethylates electrophilic centers in moderate yields (umpolung of the formaldehyde a1-reactivity), see eq. (1) and table 3.Attempted isolation, 1H- and 13C-NMR measurements, and careful product analysis of the reaction with benzaldhyde (scheme 1 and table 2) support the view that the new reagent is actually not free lithium lithiomethoxide (2) but a tin derivative, see for instance 9 in eq. (2). - The O-silylated derivative 18 (= A, R = SiMe3) is likewise generated by Sn-Li-transmetallation, but cannot be trapped externally by electrophiles due to rapid Wittig rearrangement (-> 19 -> 20).The readily accessible dilithio derivatives 21a and 23a can be employed as direct propanol and allyl alcohol d3-reagents, respectively.