232944-74-0Relevant articles and documents
Enatioselective Chalcogeno-Baylis-Hillman reaction of arylaldehydes with MVK and acrylates catalyzed by chiral thiepin-TiCl4 complex
Yin, Yan,Sun, Guofeng,Zhang, Heng,Zhou, Hong,Wu, Fanhong
, p. 365 - 369 (2014/05/20)
In a rational chiral molecular design of chalcogenides, optically active thiepin with C2-symmetric chirality was synthesized from commercially available thiophene. Then enatioselective Chalcogeno-Baylis-Hillman reactions of arylaldehydes with methyl vinyl ketone (MVK) and acrylates were investigated in the presence of thiepin-Lewis acid complex. Finally, up to 64% ee was achieved in the presence of 0.2 equiv. of (S)-thiepin at 20°C. Enatioselective Chalcogeno-Baylis-Hillman reactions between benzaldehydes and acrylates were investigated in the presence of chiral thiepin-Lewis acid complex. Finally, up to 64% ee was achieved in the presence of 0.2 equiv. of (S)-thiepin at 20°C. Copyright
Enantiodivergence in the reduction of α-methyl and α-halomethyl enones by microorganisms
De Paula, Bruno R.S.,Zampieri, Davila S.,Rodrigues, J. Augusto R.,Moran, Paulo J.S.
, p. 973 - 981 (2013/09/23)
Enones (Z)-3-methyl-(Z)-3-chloromethyl- and (Z)-3-bromomethyl-4-R-3-buten- 2-one (R = n-pentyl, phenyl, 2′- and 4′-chlorophenyl, 3′- and 4′-nitrophenyl, 4′-methoxyphenyl) were synthesized and subjected to reduction by the microorganisms Saccharomyces cerevisiae andGeotrichum candidum. Whereas the bioreduction of 3-methy-4-R-3-buten-2-ones afforded the corresponding (S)-4-R-3-methybutan-2-ones, the bioreduction of 3-chloromethyl- and 3-bromomethyl-4-R-3-buten-2-ones afforded the corresponding (R)-4-R-3-methybutan-2-ones.
FeCl3 and Yb(OTf)3 Mediated Conversion of Acetates of the Baylis-Hillman Adducts into (Z) and (E) Trisubstituted Alkenes
Krishna, Palakodety Radha,Kannan,Sharma
, p. 55 - 64 (2007/10/03)
Anhydrous FeCl3 and Yb(OTf)3 are utilised as new reagents for the stereoselective isomerisation of acetates of the Baylis-Hillman adducts to both (Z) and (E) trisubstituted alkenes respectively.
Baylis-Hillman chemistry: A novel synthesis of functionalized 1,4-pentadienes
Basavaiah, Deevi,Kumaragurubaran, Nagaswamy,Sharada, Duddu S.
, p. 85 - 87 (2007/10/03)
A novel synthesis of functionalized 1,4-pentadienes via the reaction of acrylonitrile with allyl halides, derived from Baylis-Hillman adducts, in the presence of DABCO has been described, demonstrating for the first time the application of allyl halides a
Amine and titanium (IV) chloride, boron (III) chloride or zirconium (IV) chloride-promoted Baylis-Hillman reactions
Shi, Min,Jiang, Jian-Kang,Cui, Shi-Cong
, p. 852 - 868 (2007/10/03)
The Baylis-Hillman reactions of various aryl aldehydes with methyl vinyl ketone at temperatures below -20°C using Lewis acids such as titanium (IV) chloride, boron (III) chloride or zirconium (IV) chloride in the presence of a catalytic amount of selected
Titanium(IV) chloride and oxy-compounds promoted Baylis-Hillman reaction
Shi, Min,Jiang, Jian-Kang,Cui, Shi-Cong
, p. 7343 - 7347 (2007/10/03)
The Baylis-Hillman reaction of aryl aldehydes with α,β-unsaturated ketones in the presence of titanium(IV) chloride can be promoted by oxy-compounds at room temperature, although they are not as effective as amines, chalcogenides, or quaternary ammonium salts. The oxy-compounds can be simple alcohols, ethers, and ketones. For aryl aldehydes having a strong electron-withdrawing group on the phenyl ring such as nitrobenzaldehyde or p-trifluoromethylbenzaldehyde, the chlorinated compound 1 is obtained as the major product. However, for other aryl aldehydes, the elimination compound 3 was formed predominantly. We also found that TiCl4·2THF or TiCl4·2Et2O complex is very effective for this reaction to give the chlorinated products in high yields at low temperature. A plausible mechanism is proposed.
Titanium(IV) chloride and quaternary ammonium salt promoted Baylis-Hillman reaction
Shi,Feng
, p. 406 - 411 (2007/10/03)
The Baylis-Hillman reaction of aldehydes with α,β-unsaturated ketones can be drastically affected by the reaction temperature and Lewis bases. When the reaction was carried out at -78°C using catalytic amounts of quaternary ammonium salts (R4N
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
The Baylis-Hillman reaction: An expedient synthesis of (Z)-keto allyl bromides and chlorides
Basavaiah, Deevi,Hyma, Rachakonda Suguna,Padmaja, Kisari,Krishnamacharyulu, Marimganti
, p. 6971 - 6976 (2007/10/03)
A simple and expedient synthesis of (Z)- keto allyl bromides and chlorides, from the Baylis-Hillman adducts is described.
