100281-14-9

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 32657-89-9 1,3-butadien-2-ylmagnesium chloride 
• 2244-38-4 buta-1,3-dien-2-yl-tributylstannane 
• 104-55-2 3-phenyl-propenal 
• 2219-66-1 1,4-dibromobut-2-yne 
• 121823-55-0 (4-bromo-2-butyn-1-yl)trimethylsilane 
• 18668-68-3 4-bromo-buta-1,2-diene 
• 75-11-6 diiodomethane 
• 18295-60-8 allenylmagnesium bromide 
• 84531-04-4 2-lithio-1,3-butadiene 

Relevant academic research and scientific papers

Chiral Synthesis via Organoboranes. 44. Racemic and Diastereo- and Enantioselective Homoallenylboration Using Dialkyl 2,3-Butadien-1-ylboronate Reagents. Another Novel Application of the Tandem Homologation-Allylboration Strategy

A highly general and efficient racemic and diastereo- and enantioselective homoallenylboration has been achieved with a novel boron reagent, dialkyl 2,3-butadien-1-ylboronate (dialkyl homoallenylboronate).The starting isopropyl 2,3-butadien-1-ylboronate is prepared from allenylmagnesium bromide and diisopropyl (halomethyl)boronate.This β,γ-unsaturated boronate reagent reacts readily with aldehydes via usual allylic rearrangement to give the alkyl(1,3-butadien-2-yl)methanols in excellent yields.Among the solvents examined, toluene favored enhanced reaction rates.The reaction is relatively sensitive to steric effects, so that sterically hindered aldehydes react significantly slower.Generaly, the reactivities are moderately lower than those of the corresponding simple allylboronates, possibly due to the reduced HOMO electron density of the internal double bond.Also, the reagent exhibits a unique anti diastereoselectivity in reaction with α-chiral aldehydes in contrast to the syn selectivity observed with a corresponding organosilicon reagent.However, this anti selectivity is similar to that observed for the allylboration reactions.We have successfully extended this reaction to the first general synthesis of optically active alkyl(1,3-butadien-2-yl)methanol using chiral tartrate boronate reagents with diisopropyl tartrate (DIPT) and bis(2,4-dimethyl-3-pentyl) tartrate (DMPT) as the chiral modifiers.These reagents react with aldehydes even at -78 deg C, albeit slowly, and exhibit remarkable enantioselectivity with al classes of aldehydes examined with the exception of aromatic and α-alkoxy aldehydes.Again, while the selectivity parallels that of the corresponding allylboronate, the reactivities are lower.Also, the double asymmetric homoallenylboronation of 2,3-O-isopropylidene-D-glyceraldehyde using the DMPT modified boronate reagent gives an excellent 98.5percent anti selectivity in the matched case and a moderately lower value, 82percent syn selectivity, in the mismatched case.

Synthesis of Hexahydroindenones through a Diels-Alder Cycloaddition and Nazarov Cyclization Sequence of Triene Alcohols

The Diels-Alder cycloaddition of 4-methylene-1,5-hexadien-3-ols with olefinic dienophiles such as dimethyl maleate, fumarate, and N-methylmaleimide produces 1-(1-cyclohexenyl)-2-propen-1-ols.These diene alcohols are oxidized with activated manganese(IV) o

Racemic and diastereoselective synthesis of alkyl(1,3-butadien-2-yl) methanols via a novel homoallenylboration of aldehydes with diisopropyl 2,3-butadien-1-ylboronate

Diisopropyl 2,3-butadien-1-ylboronate has been prepared by a simple method and its utility as a novel homoallenylborating reagent has been demonstrated with a series of aldehydes. Also, a high diastereoselectivity of this reagent in its reaction with an α

Asymmetrie synthesis of (1,3-butadien-2-yl)methanols from aldehydes via [1-(Silylmethyl)allenyl]methanols

[1-(Silylmethyl)allenyl]methanols 2 were efficiently synthesized from aldehydes and (4-bromobut-2-ynyl)trimethylsilane in the presence of a catalytic amount of CrCl2 and tridentate carbazole ligands. The desired compounds were obtained with good yields (43-88%) and enantioselectivities (55-78% ee). Alcohols 2 may be treated with TBAF or 2 M HCl in the case of aliphatic substrates, to provide (1, 3-butadien-2-yl)methanols 3 in 43-81% yields. This method allows the synthesis of dienes 3 with no regioselectivity problems, and it tolerates a large number of functionalities.

First regio- and enantioselective chromium-catalyzed homoallenylation of aldehydes

Game, set, and match: The first regio- and enantioselective version of the title reaction is described. The chiral catalyst prepared in situ from CrCl 3 and a non-C2-symmetric bis(oxazoline) ligand 1 affords the valuable chiral ss-al

Organometallic reactions in aqueous media. Indium-mediated 1,3-butadien-2-ylation of carbonyl compounds

(Equation Presented) Indium-mediated coupling of 1,4-dibromo-2-butyne with carbonyl compounds in aqueous media gave good yields of the 1,3-butadien-2-ylmethanols.

Regioselective buta-1,3-dienylation of aldehydes via transmetallation of 2-tributylstannylbuta-1,3-diene

Transmetallation of 2-tributylstannylbuta-1,3-diene with SnCl4 followed by Lewis base promoted addition of the resulting 1-trichlorostannyl-2,3-butadiene to aldehydes in the presence of DMF allows their buta-1,3-dienylation to take place at the

A Convenient Route to 2-Lithio-1,3-butadiene from Chloroprene via 2-Stannyl-1,3-butadiene

A convenient route to 2-lithio-1,3-butadiene from chloroprene via a 2-stannyl-1,3-butadiene is presented, and the regioselective additions to a variety of carbonyl groups are demonstrated.