108762-30-7Relevant academic research and scientific papers
Dimethyl sulfide-boron trihalide-mediated reactions of α,β-unsaturated ketones with aldehydes: One-pot synthesis of Baylis-Hillman adducts and α-halomethyl enones
Iwamura, Tatsunori,Fujita, Masaru,Kawakita, Tetsuya,Kinoshita, Sayaka,Watanabe, Shin-Ichi,Kataoka, Tadashi
, p. 8455 - 8462 (2001)
The reactions of aldehydes with 3-buten-2-one (2) were conducted in the presence of BBr3·Me2S or BCl3·Me2S and then worked up with aqueous NaHCO3, affording the α-methylene aldol 3, α-halomethyl aldol 4 or 6, and α-halomethyl enones 5 or 7, respectively. In contrast, the reactions quenched with water gave the α-halomethyl enones 5 or 7 in high yields, while the work-up with an aqueous 10% trimethylamine gave the α-methylene aldol 3. The phenol 15 and half-acetal 16 were obtained from the reaction of p-nitrobenzaldehyde (1a) with cyclohexenone (10).
2,6-diphenyl-4H-chalcogenopyran-4-ones and 2,6-diphenyl-4H- chalcogenopyran-4-thiones: A new catalyst for the Baylis-Hillman reaction
Iwama, Tetsuo,Kinoshita, Hironori,Kataoka, Tadashi
, p. 3741 - 3744 (1999)
2,6-Diphenyl-4H-chalcogenopyran-4-ones and 2,6-diphenyl-4H- chalcogenopyran-4-thiones, a new series of catalysts for the Baylis-Hillman reaction, were investigated. The reactions proceeded smoothly in the presence of 1 mol eq. of TiCl4 under at
Sulfide-BF3·OEt2 mediated Baylis-Hillman reactions
Walsh, Louise M.,Winn, Caroline L.,Goodman, Jonathan M.
, p. 8219 - 8222 (2002)
A sulfide-BF3·OEt2 mediated Baylis-Hillman reaction has been developed in which the sulfide acts via attack onto the activated alkene. The use of a chiral sulfide gives rise to Baylis-Hillman adducts with up to 53% ee.
Traditional Morita-Baylis-Hillman reaction of aldehydes with methyl vinyl ketone co-catalyzed by triphenylphosphine and nitrophenol
Shi, Min,Liu, Ying-Hao
, p. 1468 - 1470 (2006)
The development of a chiral Broonsted acid-catalyzed asymmetric Morita-Baylis-Hilman reaction of cyclone with aldehyde in the presence of triethyphosphine (PE3) was analyzed using nuclear magnetic resonance (NMR). Another catalytic system for t
Morita-baylis-hillman reaction on water without organic solvent, assisted by a 'catalytic' amount of amphiphilic imidazole derivatives
Asano, Keisuke,Matsubara, Seijiro
, p. 3219 - 3226 (2009)
A Morita-Baylis-Hillman (MBH) reaction using water as a solvent without any organic solvent can be performed by using an amphiphilic N-alkylimidazole. This reaction is accelerated by the addition of water and is the first example of a 'catalytic' MBH reaction without organic solvent in the presence of water.
A SIMPLE SYNTHESIS OF α-METHYLENE-β-HYDROXYALKANONES
Basavaiah, D.,Gowriswari, V. V. L.
, p. 2031 - 2032 (1986)
Reaction of methyl vinyl ketone with a variety of aldehydes, catalyzed by 1,4-diazabicyclo(2.2.2)octane (DABCO) in tetrahydrofuran, conveniently provides the corresponding α-methylene-β-hydroxyalkanones in good yields.
Bifunctional chiral phosphine-containing Lewis base catalyzed asymmetric Morita-Baylis-Hillman reaction of aldehydes with activated alkenes
Lei, Zhi-Yu,Liu, Xu-Guang,Shi, Min,Zhao, Meixin
, p. 2058 - 2062 (2008)
A series of novel bifunctional chiral phosphine-containing Lewis bases were synthesized and successfully applied to the asymmetric Morita-Baylis-Hillman reaction of aldehydes with methyl vinyl ketone (MVK) and ethyl vinyl ketone (EVK) to give the correspo
A highly active ionic liquid catalyst for Morita-Baylis-Hillman reaction
Lin, Yu-Sheng,Lin, Chiao-Yang,Liu, Chih-Wei,Tsai, Thomas Y.R.
, p. 872 - 877 (2006)
The Morita-Baylis-Hillman reaction is an efficient carbon-carbon bond forming reaction for the preparation of α-methylene-β-hydroxycarbonyl compounds. A new and highly active di-naphthalene imidazolium salt has been synthesized. We have found that 1,3-bis
Control of Chemo-, Regio-, and Enantioselectivity in Copper Hydride Reductions of Morita-Baylis-Hillman Adducts
Linstadt, Roscoe T. H.,Peterson, Carl. A.,Jette, Carina I.,Boskovic, Zarko V.,Lipshutz, Bruce H.
supporting information, p. 328 - 331 (2017/04/21)
Nonracemically ligated copper hydride can be used to effect tandem SN2′/1,2-reductions of racemic Morita-Baylis-Hillman (MBH) acetates to access enantioenriched chiral allylic alcohols with defined olefin geometry. MBH esters, including those w
Regioselective carbon-carbon bond cleavage in the oxidation of cyclopropenylcarbinols
Basheer, Ahmad,Mishima, Masaaki,Marek, Ilan
supporting information; experimental part, p. 4076 - 4079 (2011/10/04)
The strained double bond of cyclopropenylcarbinols undergoes a facile oxidation reaction to lead to unsaturated carbonyl derivatives. The distribution of the formed products depends on the relative stability of carbon-centered radical species, and the Sha
