112755-91-6Relevant academic research and scientific papers
A facile microwave-assisted Diels-Alder reaction of vinylboronates
Sarotti, Ariel M.,Pisano, Pablo L.,Pellegrinet, Silvina C.
supporting information; experimental part, p. 5069 - 5073 (2010/12/25)
The Diels-Alder reaction of vinylboronates can be easily performed using microwave irradiation giving excellent yields of the cycloadducts. Pinacol vinylboronate was the reagent of choice due to its stability towards hydrolysis, operational simplicity and yields of Diels-Alder products. To the best of our knowledge, this is the first example of microwave-assisted Diels-Alder reaction of boron-substituted dienophiles. Subsequent in situ oxidation of the cycloadducts with alkaline hydrogen peroxide afforded the alcohols efficiently.
Tuning of vinylborane dienophilicity. Optimization of reactivity, regioselectivity, endo stereoselectivity, and reagent stability
Singleton, Daniel A.,Martinez, Jose P.,Watson, Jose V.,Ndip, Grace M.
, p. 5831 - 5838 (2007/10/02)
Simple syntheses of some vinylboranes are reported, and their properties in Diels-Alder reactions are compared. Vinyl-3,6-dimethylborepane was the most stable simple vinylborane examined, and appears to be indefinitely stable at 25°C. Surprisingly, trivinylborane is the most reactive, and reacts about 18 times faster than the vinyldialkylboranes with cyclopentadiene. Vinyl-9-BBN is the most regioselective dienophile, in keeping with principally steric control of regioselectivity in Diels-Alder reactions of vinylboranes. All the dienophiles display high endo-stereoselectivity with piperylene, but vinyl-3,6-dimethylborepane displays significantly improved stereoselectivity with cyclopentadiene. In general, by choice of alkyl-substituents on boron, the reactivity, regioselectivity, endo-stereo selectivity, and stability of vinylboranes can be optimized.
OPTICALLY ACTIVE 2-VINYLCYCLOBUTANONES
Salaun, J.,Karkour, B.,Ollivier, J.
, p. 3151 - 3162 (2007/10/02)
Enzymatic resolution of dimethyl 2-methylsuccinate, acyloin cyclization and base induced ring contraction provided 1-hydroxycyclopropanecarboxylic acids with high optical purity (>95percent e.e).Their derivatives opened a regio- and stereoselective way to optically active 2-vinylcyclobutanones (>84-90percent e.e), providing useful building blocks for further ring expansions.
Optically active cyclopropanols from the enzymatic resolution of dimethyl α-alkylsuccinates. Synthesis of chiral 2-vinylcyclobutanones and cyclohexenones.
Salaun, Jacques,Karkour, Belkacem
, p. 4669 - 4672 (2007/10/02)
(+)-(R) dimethyl α-methylsuccinates, obtained by the enantioselective hydrolysis of the racemic diester by porcine pancreatic lipase, undergo acyloin cyclization followed by stereoselective ring contraction to provide 1-alkenylcyclopropanols
