Synthesis of homoallylic (but-3-enylic) alcohols from aldehydes with allylic chlorides, tin(II) chloride and potassium iodide in water
Homoallylic (but-3-enylic) alcohols have been prepared in good yields by reductive allylation of aldehydes in water with various allylic chlorides in the presence of tin(II) chloride and potassium iodide. The Barbier type reaction with prop-2-ynyl chloride is also achieved under the same conditions.
Houllemare, Didier,Outurquin, Francis,Paulmier, Claude
p. 1629 - 1632
(2007/10/03)
Indium mediated reactions in water: Synthesis of β-hydroxyl esters
A variety of β-hydroxyl esters were synthesized efficiently through indium mediated carbon-carbon bond formation in water followed by ozonolysis.
Yi, Xiang-Hui,Meng, Yue,Li, Chao-Jun
p. 4731 - 4734
(2007/10/03)
Process for producing propargylcarbinol compounds
The present invention provides a process for producing a propargylcarbinol compound of formula (I): STR1 where R1 and R2 are as defined herein. The process comprises reacting a haloallycarbinol compound of formula (II) with a base. The present invention also relates to a process for producing the haloallylcarbinol compound. The above propargylcarbinol compound is useful as an intermediate for agrochemicals, pharmaceuticals, perfumes, resin monomers, and the like.
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(2008/06/13)
An Efficient Synthesis of 3-Chlorohomoallyl Alcohols. Zinc-Promoted 2-Chloroallylation of Carbonyl Compounds with 2,3-Dichloropropene in an Aqueous Solvent System
In the presence of metallic zinc, 2,3-dichloropropene has been found to react smoothly with a variety of carbonyl compounds in an aqueous solvent system to give the corresponding 3-chlorohomoallyl alcohols in excellent yields. Key words: 2-Chloroallylatio
Oda, Yoshiaki,Matsuo, Sanshiro,Saito, Kenji
p. 97 - 100
(2007/10/02)
Highly Selective Carbon-Carbon Bond Forming Reactions Mediated by Chromium(II) Reagents
A low valent chromium reagent is generated from chromium(III) chloride and a half mol of lithium aluminum hydride in tetrahydrofuran.The reagent behaves similarly to anhydrous chromium(II) chloride, which is commercially available, and reduces allylic halides to produce unisolable allylchromium species which add efficiently to aldehydes or ketones with high degree of stereo- and chemoselectivity.Particularly, high threo selectivity is observed in the reaction of aldehydes and 1-bromo-2-butene and is ascribed to a chair-like six-membered transition state.Simple reduction od allylic and benzylic halides produces biallyls and bibenzyls, while gem-dibromocyclopropanes afford the corresponding allenes in excellent yields.