73786-25-1

Upstream product

• 94762-80-8 2,3-bis(3,4-dimethoxyphenyl)butane-2,3-diol 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 197244-15-8 but-2-yne-1,4-diyl dimethyl bis(carbonate) 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 109669-47-8 <1-(3,4-dimethoxyphenyl)ethen-1-yl>tributylstannate 

Downstream Products

• 73786-27-3 (1R,5S,7S,8R)-8-Bromo-7,8-bis-(3,4-dimethoxy-phenyl)-10-oxa-1-azonia-tricyclo[5.2.1.0^1,5]decane; bromide 
• 73786-28-4 (1aR,2aR,6aR)-1a,6a-Bis-(3,4-dimethoxy-phenyl)-octahydro-1-oxa-5a-aza-cyclopropa[f]indene 
• 74170-42-6 (R)-2,3-Bis-(3,4-dimethoxy-phenyl)-1-(R)-pyrrolidin-2-yl-but-3-en-2-ol 
• 5385-61-5 4,4'-(ethene-1,1-diyl)bis(1,2-dimethoxybenzene) 
• 26503-67-3 (+/-)-6,7-di(3,4-dimethoxyphenyl)-1,2,3,5,8,8a-hexahydro-indolizine 

Relevant academic research and scientific papers

Pd(0)-catalysed formation of diarylated dienes from propargyl carbonates and organoboron and organotin(IV) reagents

The 1,1-dimethylbutyne-1,4-diol derivative 1 reacts with 2 mol. equiv. of organoboron (NaBPh4 arylboronic acids) and organotin(IV) reagents to give 1,1-dimethyl-2,3-disubstituted butadienes in good yield via allenylpalladium(II) and vinylidene-π-allylpalladium(II) intermediates. Unsubstituted esters 6 and butyne dicarbonate 7 lead to symmetrical dienes 8.

Formation of 1,3-Diynes, 1,3-Dienes, and Biphenyls via the Copper(II) Nitrate Mediated Coupling of Organotin Compounds

A method for the preparation of symmetrically substituted 1,3-diynes, 1,3-dienes, and biphenyls based on the copper(II) nitrate mediated coupling of organotin compounds 1 (R = alkynyl, alkenyl, aryl) is described.The addition of alkynylstannane 1a, 1b, or 1c (a, R = THPOCH2C; b, R = n-C4H9CC; c, R = C6H5C) to 1 equiv of Cu(NO3)2*3H2O in THF at 23 deg C afforded 1,3-diynes 2a-c in 85percent, 60percent, and 50percent yield, respectively.Similar treatment of alkenylstannanes 1d, 1e, 1f, or 1g (d, R = ; e, (E)-PhCH2OCH2CH=CH; f, (Z)-PhCH2OCH2CH=CH; g, 3,4-(CH3O)2C6H3C(=CH2)) afford to the 1,3-dienes 2d-g in 80percent, 72percent, 75percent, and 71percent yield, respectively.In the case of (E)- or (Z)-vinylstannanes, the dimerization process is found to be highly stereospecific.For example, copper(II) nitrate induced coupling of 1f (R = (Z)-PhCH2OCH2CH=CH) afforded a 23:1 ratio of (Z,Z)/(E,Z)-diene stereochemistry for 2f (R = PhCH2OCH2CH=CH).Also prepared by this method were the substituted biphenyls 2h-k (h, R = 4-CH3C6H4; i, R = 4-CH3OC6H4; j, R = 2-CH3OC6H4; k, R = 4-(CH3)-2,6-(CH3O)2C6H3) in 14-66percent yield.Aspects about the possible mechanism of dimerization are discussed.

SYNTHESIS OF dl-SEPTICINE

Cyloaddition reaction of 1-pyrroline 1-oxide with 2,3-bis(3,4-dimethoxyphenyl)butadiene proceeded regioselectively to give two stereoisomeric isoxazolidine derivatives, one of which was converted into septicine by three-step reactions.