129139-66-8Relevant academic research and scientific papers
Lithium alkoxide-promoted michael reaction between silyl enolates and α,β-unsaturated carbonyl compounds
Mukaiyama, Teruaki,Tozawa, Takashi,Fujisawa, Hidehiko
, p. 1410 - 1411 (2007/10/03)
Michael reaction between silyl enolates and α,β-unsaturated carbonyl compounds by using a catalytic amount of Lewis base such as lithium alkoxide in DMF proceeds smoothly to afford the corresponding Michael-adducts in good yields with moderate to high diastereoselectivities. This reaction can be reasonably explained by considering an alkoxide anion-initiated autocatalytic process.
Magnesium Chloride-Promoted Michael Addition of Dimethylsilyl Enolates to α-Enones
Miura, Katsukiyo,Nakagawa, Takahiro,Hosomi, Akira
, p. 2068 - 2070 (2007/10/03)
In the presence of MgCl2, dimethylsilyl (DMS) enolates 1 smoothly reacted with α-enones in DMF to form 1,5-diketones 3 in moderate to high yields. The Michael addition proceeded with moderate to high anti-diastereoselectivity.
Indium-trichloride catalyzed Michael reaction of silyl enol ethers with α,β-unsaturated carbonyl compounds under neat condition
Loh, Teck-Peng,Wei, Lin-Li
, p. 7615 - 7624 (2007/10/03)
In the presence of a catalytic amount of indium (III) trichloride (InCl3) (20 mol%), ketene silyl enol ethers react quickly with α, β- unsaturated ketones and esters to afford the corresponding Michael adducts in moderate to good yields. Indium(III) trichloride can be recovered and reused without decrease in yields.
Novel Reactive Silyl Enolates. Highly Stereoselective Aldol and Michael Reactions without Catalysts
Kobayashi, Shu,Nishio, Koichi
, p. 2647 - 2649 (2007/10/02)
Novel silyl enolates, prepared in situ from ketones and dimethylsilyl ditriflate (Me2Si(OTf)2) in the presence of a tertiary amine, reacted smoothly with electrophiles such as aldehydes, acetals, or α,β-unsaturated ketones without catalyst at -78 deg C to
Stereoselective Michael additions of titanium "ate" complexes of ketone and ester enolates
Bernardi, Anna,Dotti, Pierfranco,Poli, Giovanni,Scolastico, Carlo
, p. 5597 - 5606 (2007/10/02)
The conjugate addition of Ti "ate" complexes of ketone and ester enolates to α,β-unsaturated carbonyl compounds was studied. The reaction was found to be highly regio- and stereoselective. Compared to the lithium enolates, ketone enolate Ti complexes show
New role of tin(II) compounds in organic synthesis
Mukaiyama, Teruaki,Kobayashi, Shu
, p. 39 - 52 (2007/10/02)
Three new carbon-carbon bond forming reactions by the use of new catalyst systems involving tin(II) compounds are described in this article.The aldol reaction of silyl enol ethers with acetals or aldehydes and the Michael reaction of silyl enol ethers wit
Effective Activation of Carbonyl and Related Compounds with Phosphonium Salts. The Aldol and Michael Reactions of Carbonyl Compounds with Silyl Nucleophiles and Alkyl Enol Ethers
Mukaiyama, Teruaki,Matsui, Shigekazu,Kashiwagi, Kouichi
, p. 993 - 996 (2007/10/02)
In the presence of a catalytic amount of a phosphonium salt, aldol reaction of silyl enol ethers with aldehydes or acetals and the Michael reaction of silyl enol ethers with α,β-unsaturated ketones or acetals proceed smoothly to afford the corresponding a
A Convenient Method for the Preparation of Secondary Propargylic Ethers. The Reaction of Acetals with 1-Trimethylsilyl-1-alkynes Promoted by the Combined Use of Catalytic Amounts of Tin(IV) Chloride and Zinc Chloride
Hayashi, Masaji,Inubushi, Atsuro,Mukaiyama, Teruaki
, p. 4037 - 4042 (2007/10/02)
In the coexistence of catalytic amounts of SnCl4 and ZnCl2, acetals undergo a coupling with 1-trimethylsilylalkynes to give secondary propargilic ethers in good yields.Similarly, propargilic ethers are directly produced from aldehydes by the treatment with alkoxytrimethylsilanes and 1-trimethylsilylalkynes under the same conditions.This catalyst system also efficiently promotes aldol reaction of silyl enol ethers with acetals or aldehydes, and the Michael reaction of silyl enol ethers with α,β-unsaturated ketones.
An Essentially Mild and Efficient Catalyst System for the Activation of Carbonyl Compounds and Their Derivatives. The Combined Use of Trimethylsilyl Chloride and Tin(II) Chloride
Iwasawa, Nobuharu,Mukaiyama, Teruaki
, p. 463 - 466 (2007/10/02)
An essentially mild and efficient catalyst system, the combined use of trimethylsilyl chloride and tin(II) chloride, is effectively employed for the activation of acetals, aldehydes, orthoesters, and α,β-unsaturated ketones to accomplish the reaction with
