Asymmetric 1,3-Dipolar Cycloaddition Reactions of Azomethine Imines with Acrolein Catalyzed by L-Proline and Its Derivatives
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...
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...
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We provide a comprehensive account of the 1,3-dipolar cycloaddition reactions of azomethine ylides with carbonyl dipolarophiles. Many different azomethine ylides have been studied, including stabilized and non-stabilized ylides. Of the carbonyl dipolarophiles, aldehydes including formaldehyde are the most studied, although there are now examples of cycloadditions with ketones, ketenes and carbo...
متن کاملRhodium(II)-Catalyzed 1,3-Dipolar Cycloaddition Reactions
The rhodium(II)-catalyzed formation of 1,3-dipoles has played a major role in facilitating the use of the dipolar cycloaddition reaction in modern organic synthesis. This is apparent from the increasing number of applications of this chemistry for the construction of heterocyclic and natural product ring systems. This chapter initially focuses on those aspects of rhodium(II) catalysis that cont...
متن کاملBifunctional AgOAc-catalyzed asymmetric [3 + 2] cycloaddition of azomethine ylides.
[reaction: see text] A bifunctional AgOAc-catalyzed asymmetric cycloaddition of azomethine ylides with electronic-deficient alkenes was developed using ferrocenyloxazoline-derived N,P ligands. The reactive metal-bound azomethine ylide dipole is formed by the deprotonation with acetate, and extra base is not necessary. The reactions proceed with high enantioselectivity. This method provides an e...
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ژورنال
عنوان ژورنال: HETEROCYCLES
سال: 2010
ISSN: 0385-5414
DOI: 10.3987/com-10-11967