Jing-Yao Zhou

A New Approach for the Synthesis of α-Methylene-γ-Butyrolactones from α-Bromomethyl Acrylic Acids (or Esters)

Abstract This paper reports that a new approach for the synthesis of α-methylene-γ-butyrolactones from the reaction of α-bromomethyl acrylic acid (or ester), powdered tin and carbonyl compounds in one pot with excellent to good yields.

Barbier-Type Allylation of Aldehydes and Ketones with Metallic Lead in Aqueous Media

Abstract Homoallylic alcohols can be obtained from allylation of aldehydes and ketones with allyl bromide promoted by metallic lead. These reactions can be carried out smoothly in aqueous media.

Allylation of Aldehydes and Ketones with Allyl Bromide and Tin Promoted by Me3SiCI and Alcohol

Abstract Allylation of aldehydes and ketones to give homoallylic alcohols can be carried out successfully with allyl bromide and metallic tin under anhydrous condition. The 64–89% yields of homoallyl alcohols are obtained by addition of chlorotrimethylsilane as a promoter in anhydrous methanol.

Highly Selective Synthesis of Acetylenic Alcohols Promoted by Metallic Dysprosium in the Presence of Mercuric Chloride

Abstract Promoted by metallic dysprosium, carbonyl compounds react smoothly with propargyl bromide to afford the corresponding homopropargylic alcohols in good to excellent yields without observation of allenic alcohols. In addition, this reaction is regioselective and chemoselective.

Lead-Promoted 2-Carboethoxyallylation or 2-Carboxylallylation of Aldehydes: A New and Facile Method for the Synthesis of α-Methylene-γ-Butyrolactones

Abstract In the presence of powdered lead, the reaction of aldehydes and α-bromomethylacrylate (or α-bromomethylacrylic acid) can be carried out under mild condition, the products 4-hydroxy-2-methylenebutanoates (or 4-hydroxy-2-methylenebutanoic acids) can be easily converted to α-methylene-γ-butyrolactones in the presence of CF3COOH.

ALLYLATION OF ESTERS PROMOTED BY METALLIC DYSPROSIUM IN THE PRESENCE OF MERCURIC CHLORIDE

ABSTRACT In the presence of mercuric chloride, the reactions of esters with allyl bromide and metallic dysprosium in anhydrous THF give diallyl alkyl carbinols in good yields. When γ-butyrolactone is used as the substrate, the corresponding product is 4-allyl-6-heptene-1, 4-diol.

Tin-promoted stereocontrolled intramolecular allylation of carbonyl compounds: a facile and stereoselective method for ring construction

The intramolecular allylation of carbonyl compounds 1 promoted by metallic tin proceeds in a stereocontrolled manner to give cyclic products 2 with high diastereoselectivity.

Metallic dysprosium promoted allylation of carbonyl compounds in the presence of mercuric chloride

Dysprosium metal promoted Barbier-type allylation of ketones and aldehydes has been investigated. It has been shown that dysprosium metal (activated by mercuric chloride) is effective in promoting the reaction of ketones with allyl iodide. The corresponding homoallylic alcohols are obtained in satisfactory yields. This reaction is regioselective and chemoselective. An α, β-unsaturated ketone affords a 1,2-addition product selectively. Reactive groups (such as Cl, Br, and methoxy) of aromatic ketones remain unchanged under the reaction conditions.

Study on the “Tin-Ene” reaction of α-bromoacetophenone and metallic tin with aldehydes

Abstract β-hydroxy ketones were obtained in good yields by the “tin-ene” reactions of α-bromoacetophenone and metallic tin with aldehydes.

Diastereoselective Reaction of Aldehydes with 3-Bromocyclohexene and Tin

Abstract The reaction of 3-bromocyclohexene and powdered tin with aromatic aldehydes and an alkynal provides excellent erythro-selective products, while the corresponding reactions with aliphatic aldehydes proceed with moderate erythro-selectivity.