A Highly Enantio- and Diastereoselective Cu-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with Nitroalkenes
نویسندگان
چکیده
منابع مشابه
Cu(I)-catalyzed highly exo-selective and enantioselective [3 + 2] cycloaddition of azomethine ylides with acrylates.
[reaction: see text] A novel Cu(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with acrylates has been developed. Up to 98/2 exo/endo selectivity and up to 98% enantiomeric excess have been achieved.
متن کاملAsymmetric 1,3-dipolar cycloadditons of stabilized azomethine ylides with nitroalkenes.
This review highlights the biological importance of many polysubstituted nitro-prolines and -pyrrolidines. Their preparation using asymmetric 1,3-dipolar cycloadditions of azomethine ylides with nitroalkenes using diastereoselective and enantioselective strategies is described remarking the scope and main features of each one.
متن کاملAsymmetric construction of trifluoromethylated pyrrolidines via Cu(I)-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with 4,4,4-trifluorocrotonates.
Trifluoromethylated pyrrolidines have been synthesized via catalytic asymmetric 1,3-dipolar cycloaddition with excellent stereoselectivity for the first time. Epimerization of the endo-pyrrolidines obtained from cis-4,4,4-trifluorocrotonate into the exo-pyrrolidines was also revealed.
متن کاملDiastereoselective 1,3-dipolar cycloaddition of pyrylium ylides with chiral enamides.
Chiral enamides 5f-i were found to react with pyrylium ylides to give cycloadducts 6d-i in good yields with an excellent level of stereoselectivity. The chiral auxiliary was successfully removed on hydrogenolysis of compound 6f in continuous flow (H-Cube) resulting in the first asymmetric synthesis of complex amine 8.
متن کاملTheoretical study of the highly diastereoselective 1,3-dipolar cycloaddition of 1,4-dihydropyridine-containing azomethine ylides to [60]fullerene (Prato's reaction).
The 1,3-dipolar cycloaddition of azomethine ylides bearing the biologically active 1,4-dihydropiridine ring to C(60) was investigated by means of quantum mechanical calculations at the semiempirical AM1 and DFT (B3LYP/6-31G) methods. The presence of two chiral centers and one chiral axis in the resulting fulleropyrrolidines leads to four possible [6,6] cycloaddition products. Formation of atrop...
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ژورنال
عنوان ژورنال: Angewandte Chemie International Edition
سال: 2006
ISSN: 1433-7851,1521-3773
DOI: 10.1002/anie.200690065