Catalytic Enantioselective Desymmetrization of 1,3-Diazido-2-propanol via Intramolecular Interception of Alkyl Azides with Diazo(aryl)acetates

The first catalytic enantioselective desymmetrization of 1,3-diazido-2-propanol via an intramolecular interception of alkyl azides by Cu–carbenoids has been realized. A wide range of 1,3-diazidoisopropyl diazo­(aryl)­acetates were converted to cyclic α-imino esters in the presence of bisoxazoline ligand (<i>S,S</i>)-Ph-Box with good to excellent yields, and the enantiomeric excess was up to 97%

Catalytic Enantioselective Desymmetrization of 1,3-Diazido-2-propanol via Intramolecular Interception of Alkyl Azides with Diazo(aryl)acetates

The first catalytic enantioselective desymmetrization of 1,3-diazido-2-propanol via an intramolecular interception of alkyl azides by Cu–carbenoids has been realized. A wide range of 1,3-diazidoisopropyl diazo­(aryl)­acetates were converted to cyclic α-imino esters in the presence of bisoxazoline ligand (<i>S,S</i>)-Ph-Box with good to excellent yields, and the enantiomeric excess was up to 97%

Correction to Catalytic Enantioselective Desymmetrization of 1,3-Diazido-2-propanol via Intramolecular Interception of Alkyl Azides with Diazo(aryl)acetates

Correction to Catalytic Enantioselective Desymmetrization of 1,3-Diazido-2-propanol via Intramolecular Interception of Alkyl Azides with Diazo(aryl)acetate

Catalytic Enantioselective Desymmetrization of 1,3-Diazido-2-propanol via Intramolecular Interception of Alkyl Azides with Diazo(aryl)acetates

The first catalytic enantioselective desymmetrization of 1,3-diazido-2-propanol via an intramolecular interception of alkyl azides by Cu–carbenoids has been realized. A wide range of 1,3-diazidoisopropyl diazo­(aryl)­acetates were converted to cyclic α-imino esters in the presence of bisoxazoline ligand (<i>S,S</i>)-Ph-Box with good to excellent yields, and the enantiomeric excess was up to 97%

Enantioselective Preparation of <i>cis</i>-β-Azidocyclopropane Esters by Cyclopropanation of Azido Alkenes Using a Chiral Dirhodium Catalyst

A diastereo- and enantiocontrolled preparation of the conformationally restricted <i>cis</i>-β-azidocyclopropane esters have been developed. The Rh₂(<i>S</i>-DOSP)₄ was found to be an efficient catalyst in hexane for the cyclopropanation of azido alkenes with diazo esters, and 19 <i>cis</i>-β-azidocyclopropane esters were prepared in excellent yields. The value of the diastereomer ratio was up to 99:1, and the enantiomeric excess was up to 95%. Furthermore, the relative and absolute configuration was confirmed by X-ray analysis

Enantioselective Preparation of <i>cis</i>-β-Azidocyclopropane Esters by Cyclopropanation of Azido Alkenes Using a Chiral Dirhodium Catalyst

A diastereo- and enantiocontrolled preparation of the conformationally restricted <i>cis</i>-β-azidocyclopropane esters have been developed. The Rh₂(<i>S</i>-DOSP)₄ was found to be an efficient catalyst in hexane for the cyclopropanation of azido alkenes with diazo esters, and 19 <i>cis</i>-β-azidocyclopropane esters were prepared in excellent yields. The value of the diastereomer ratio was up to 99:1, and the enantiomeric excess was up to 95%. Furthermore, the relative and absolute configuration was confirmed by X-ray analysis