107486-95-3Relevant academic research and scientific papers
Stereoselective synthesis of 1,2,3-triol derivatives from α,β-unsaturated acylsilanes
Honda, Mitsunori,Nakamura, Takayoshi,Sumigawa, Takumi,Kunimoto, Ko-Ki,Segi, Masahito
, p. 565 - 577 (2015/02/05)
The stereoselective synthesis of 1,2,3- triol derivatives having contiguous stereogenic centers from α,β-unsaturated acylsilanes 1 was described. The oxidation of an olefin moiety of 1 with osmium tetroxide proceeded smoothly to give the corresponding 2,3- syn-dihydroxyacylsilanes 2. The protection of two hydroxy groups of 2 followed by a nucleophilic reaction to the silyl carbonyl group gave the corresponding silylated triol derivatives (7 and 8) with high stereoselectivity, depending on the kind of nucleophilic reagents. The deprotection for 7 and 8 and the following protodesilylation gave two isomers of possible four 1,2,3- triol derivatives. The stereoselective triol synthesis by asymmetric diolization of α-silylated allyl alcohols 11 derived by nucleophilic addition to 1 was also investigated.
Synthesis of β-Alkoxy Ketones and α′-Functionalized β-Alkoxy Ketones Utilizing Benzotriazole-Stabilized Acyl Anion Synthons
Katritzky, Alan R.,Feng, Darning,Qi, Ming
, p. 1473 - 1477 (2007/10/03)
1-(α-Alkoxyalkyl)benzotriazoles 1a-d add to phenyl vinyl ether to form key intermediates 4a-d, which readily undergo lithiation and subsequent trapping by a variety of electrophiles to give the expected substituted derivatives 7a-d, 9a-c, 11, 13, 15, and 18 in high yields. Subsequent hydrolysis of these compounds provides a novel high-yield acyl anion synthon approach for the synthesis of β-alkoxy ketones 8 or α′-functionalized β-alkoxy ketones 10, 12, 14, 16, and 19 by short procedures from readily available starting materials.
A Conjugate Addition-Elimination Route to Alkenoyltrimethylsilanes
Cunico, Robert F.,Zhang, Cui-ping
, p. 9823 - 9838 (2007/10/02)
Monosubstitution of 3,3-dichloro-1-(trimethylsilyl)-2-propenone (1) with organocuprates stereoselectively affords E-3-alkyl- and Z-3-phenyl-3-chloro-1-(trimethylsilyl)-2-propenones.Further substitution proceeds stereoselectively as a function of extant and incoming substituents. 1 was also reduced to E-3-chloro-1-(trimethylsilyl)-2-propenone and the latter converted to E-3-alkyl- and E-3-phenyl-1-(trimethylsilyl)-2-propenones.
A novel synthesis of acylsilanes
Nakada, Masahisa,Nakamura, Sei-Ichi,Kobayashi, Susumu,Ohno, Masaji
, p. 4929 - 4932 (2007/10/02)
A mild and general preparative method for acylsilane is presented. This novel method can be applied without any difficulty to α-chiral, α-alkoxy and multifunctionalized compounds.
REACTION OF 1-TRIMETHYLSILYLCYCLOPYLLITHIUM DERIVATIVES WITH DICHLOROMETHYL METHYL ETHER. A NOVEL SYNTHESIS OF CYCLOPROPYL SILYL KETONES
Nakajima, Tadashi,Tanabe, Masaru,Ohno, Katsuhiko,Segi, Masahito,Suga, Sohei
, p. 177 - 180 (2007/10/02)
Treatment of 1-trimethylsilylcyclopropyllithium derivatives with dichloromethyl methyl ether affords the corresponding new cyclopropyl silyl ketones in moderate yield.This reaction involves the intramolecular 1,2-silicon shift from carbon to carbon.
