292634-18-5Relevant academic research and scientific papers
Synthesis of chiral phosphorus reagents and their application in combination with lewis acid as a cocatalyst in morita-baylis-hillman reaction
Tang, Hongying,Cheng, Xiamin,Zhang, Zhongbiao
experimental part, p. 8 - 15 (2012/03/26)
Two novel chiral thiophosphoramides and two chiral phosphoramidites were synthesized starting from (S)-α-phenylethylamine and (R)-(+) or (S)-(-)-1,1'-Bi-2-naphthol (BINOL), respectively, and their application in combination with Lewis acid as cocatalysts in asymmetric Morita-Baylis-Hillman (MBH) reaction was investigated. Dramatic rate acceleration (the corresponding adducts were obtained in fair to excellent chemical yield within 15 min-5 h) was observed in these chiral phosphorus reagents/Lewis acid cocatalyzed MBH reaction between 4-nitrobenzaldehyde and activated alkenes, and in one case, moderate enantioselectivity was achieved (the corresponding adduct's ee value is 44%). Copyright Taylor and Francis Group, LLC.
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 (2007/10/03)
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).
Amendment in titanium(IV) chloride and chalcogenide-promoted Baylis- Hillman reaction of aldehydes with α,β-unsaturated ketones
Shi, Min,Jiang, Jian-Kang
, p. 4793 - 4797 (2007/10/03)
The Baylis-Hillman reaction can be drastically affected by the reaction temperature and Lewis base. When the reaction was carried out at -20°C using methyl sulfide as a Lewis base in the presence of titanium(IV) chloride, the chlorinated compound 1 was
