Weiyu Ding

A Highly Stereoselective Synthesis of 2,3,4,5‐Tetrasubstituted‐trans‐2,3‐dihydrofurans

Abstract α,β‐Unsaturated sulfones derivatives 5 was prepared from sodium p‐toluenesulfinate (1) and the products reacted with substituted‐carbomethoxymethyltriphenylarsonium bromide 6 in the presence of potassium carbonate at room temperature to give cyclopropane derivatives 2‐substituted‐3‐substitutedphenyl‐4‐p‐toluenesulfonyl‐5‐phenyl‐trans‐2,3‐dihydrofurans 7 and/or 8 with high stereoselectivity.

Solvent-free stereoselective synthesis of cis-1-carbomethoxy-2-aryl-3,3-dicyanocyclopropanes by grinding

Abstract The novel route of high stereoselective synthesis of cis‐1‐carbomethoxy‐2‐aryl‐3,3‐dicyanocyclopropanes by grinding is described. This process is simple, efficient, and environmentally benign.

Stereoselective Synthesis of cis‐1‐Aryl‐2‐benzoyl‐3,3‐dicyanocyclopropanes in the Presence of KF·2H2O

Abstract KF · 2H2O was found to be a highly efficient base for synthesis of cis‐1,2‐cyclopropanes with arsonium salt and olefins. The advantages of the process are mild reaction condition, easy workup, excellent yields, and high stereoselectivity.

Stereoselective synthesis of cis-1-carbomethoxy-2-aryl-3,3-dicyanocyclopropanes

ABSTRACT The route of preparing of 1-carbomethoxy-2-aryl-3,3-dicyanocyclopropanes through the reaction of arylidenemalononitrile with methoxycarbonylmethyltriphenylarsonium bromide in the presence of K2CO3 under mild conditions with high yield and stereoselectivity is described.

STEREOSELECTIVE SYNTHESIS OF TRANS-β-METHOXYCARBONYL-γ-ARYL-γ-BUTYROLACTONES

ABSTRACT Stereoselective synthesis of trans-β-methoxycarbonyl-γ-aryl-γ-butyrolactones (5) by the reaction of methoxycarbonylmethyl triphenyl arsonium bromide (1) and 2,2-dimethyl-5-substituted-benzal-1,3-dioxa-4,6-dioxa-4,6-dione (2) is carried out in the presence of potassium carbonate and trace water in dimethoxyethane. 1,2-Cis-cyclopropane 3 is formed as an intermediate. The stability of compound 3 in water is related to the property of the aryl substituent. With strong electron-donating groups [2a–c, Ar=4-CH3O‒C6H4; 3,4-OCH2O‒C6H3 or 4-(CH3)2N‒C6H4] at room temperature 3 is formed in situ and transformed to γ-butyrolactones 5a–c immediately, whereas when the aryl substituent is H or a weak electron-donating or electron-withdrawing group (2d–g, Ar=4‒CH3-C6H4; C6H5; 4-Cl‒C6H4 or 4-NO2‒C6H4), 3 is stable to water at room temperature. On further heating in acetone, 3 is transformed to γ-butyrolactones 5d–g (stepwise synthesis). One-pot synthesis of 5d–g from the reaction of 1 with 2d–g is also studied.

An Efficient and Highly Stereoselective Synthesis of CIS-1-Acetyl-2-Aryl-6,6-Dimethyl-5,7-Dioxo-Spiro-[2,5]-4,8-Octadiones and β,γ-Trans-β-Acetyl-γ-Aryl-Butyrolactones

Abstract Acetylmethyltriphenylarsonium bromide 6 in the presence of potassium carbonate and trace water reacted with 2,2-dimethyl-l,3-dioxa-5-substituted-benzylidene-4,6-dione 2 at room temperature to give cyclopropane derivatives cis-l-acetyl-2-aryl-6,6-dimethyl-5,7-dioxospiro-[2,5]-4,8-octadiones 7 (X=p-CH3, p-Cl, H, p-NO2) or β,γ-trans-β-acetyl-γ-aryl-γ-butyrolactones 8 (X=p-CH3O, p-N(CH3)2, 3′,4′-OCH2O-) with good yield and high stereoselectivity.

Study on the Reaction of CIS-1-Acetyl-2-Aryl-6,6-Dimethyl-5,7-Dioxospiro-[2,5]-4,8-Octadiones with Methanol

Abstract Cis-l-acetyl-2-aryl-6,6-dimethyl-5,7-dioxo-spiro-[2,5]-4,8-octadiones 3a-d (X=p-CH3, p-Cl, H, p-NO2) reacted with anhydrous methanol in a sealed tube at 80°C to form trans, cis-α-carbomethoxy-β-(α′-methoxy-α′-aryl)-γ-methoxy-γ-methyl-γ-butyrolactones 4a-d and cis, cis-α-carbomethoxy-β-(α′-methoxy-α′-aryl)-γ-methoxy-γ-methyl-γ-butyrolactones 5a-d in good yield.

Stereoselective synthesis of cis-1-aryl-2-benzoyl-3,3-dicyanocyclopropanes in water

Abstract The highly stereoselective preparation of cis‐1‐aryl‐2‐benzoyl‐3,3‐dicyanocyclopropanes with arsonium salt and olefin in water is described. It is simple, efficient, and environmentally benign.

THE STEREOSELECTIVE SYNTHESIS OF N-ARYL-TRANS, TRANS-α-CARBOXYL-β-METHOXYCARBONYL-γ-ARYL-γ-BUTYROLACTAMS

Cis-1-methoxycarbonyl-2-aryl-6,6-dimethyl-5,7-diox-spiro-[2,5]-4,8-octadiones (1) in dimethyl ethylene glycol at room temperature react with anilines (2) to give N-aryl-trans,trans-α-carboxyl-β-methoxycarbonyl-γ-aryl-γ-butyrolactams (3) in good to excellent yields and high stereoselectivity.

An Efficient and Highly Stereoselective Synthesis of β,γ-Trans-β-Benzoyl-γ-Aryl-γ-Butyrolactones

Abstract Benzoylmethyltriphenylarsonium bromide 6 in the presence of potassium carbonate reacted with 2,2-dialkyl-1,3-dioxa-5-substituted-benzylidene-4,6-dione 2 at room temperature to give β,γ-trans-β-benzoyl-γ-aryl-γ-butyrolactones 7 in good yield.