Thermal [3+2] Cycloaddition of Aromatic Azomethine Imines with Allenoates
نویسندگان
چکیده
منابع مشابه
Group 11 metal amide-catalyzed asymmetric cycloaddition reactions of azomethine imines with terminal alkynes.
We developed a 1,3-dipolar cycloaddition reaction of azomethine imines with terminal alkynes catalyzed by group 11 metal amides to provide N,N-bicyclic pyrazolidinone derivatives. This reaction afforded the cycloadducts in a unique 5,7-disubstituted manner. Furthermore, we succeeded in applying this catalysis to asymmetric reactions, and the desired heterocycles were produced in high yields wit...
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[3+2] Cycloaddition of azomethine imines with electron-deficient terminal alkynes was smoothly catalyzed by a chiral bis(imidazolidine)pyridine-CuOAc complex to give bicyclic pyrazolo[1,2-a]pyrazolone derivatives with up to 74% ee.
متن کاملStereoselective Lewis base catalyzed formal 1,3-dipolar cycloaddition of azomethine imines with mixed anhydrides.
Stereoselective synthesis of pyrazolidinones via dipolar cycloaddition of azomethine imines with active esters under Lewis base catalysis is presented. The active esters are readily generated in situ from the corresponding acids. Products, which are obtained with excellent diastereocontrol and high enantioselectivity, contain along with the pyrazolidinone core also the tetrahydroisoquinoline st...
متن کاملN-heterocyclic carbene-catalyzed [3+4] cycloaddition and kinetic resolution of azomethine imines.
The first N-heterocyclic carbene (NHC)-catalyzed [3+4] cycloaddition of azomethine imines and enals is disclosed. Oxidative catalytic remote activation of enals affords 1,4-dipolarophile intermediates that react with 1,3-dipolar azomethine imines to generate dinitrogen-fused seven-membered heterocyclic products with high optical purities. Our approach also provides effective kinetic resolution ...
متن کامل[4+3] Cycloaddition of in situ generated azoalkenes with C,N-cyclic azomethine imines: efficient synthesis of tetrazepine derivatives.
An unprecedented [4+3] cycloaddition of in situ generated azoalkenes with C,N-cyclic azomethine imines has been developed without the use of any catalyst, providing an efficient and mild approach to synthesise highly functionalized 1,2,4,5-tetrazepine derivatives in high yields (76-92%).
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ژورنال
عنوان ژورنال: Synthesis
سال: 2012
ISSN: 0039-7881,1437-210X
DOI: 10.1055/s-0032-1316822