A new copper-catalyzed [3 + 2] cycloaddition: enantioselective coupling of terminal alkynes with azomethine imines to generate five-membered nitrogen heterocycles.
نویسندگان
چکیده
A copper-catalyzed method for the regioselective 1,3-dipolar cycloaddition of azomethine imines to terminal alkynes has been developed. Through the use of a chiral phosphaferrocene-oxazoline ligand, a wide range of substrates can be coupled to generate useful heterocycles in very good enantiomeric excess.
منابع مشابه
Chiral bis(imidazolidine)pyridine-cu complex-catalyzed enantioselective [3+2]-cycloaddition of azomethine imines with propiolates.
[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.
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A strategy for exo and enantioselective 1,3-dipolar cycloaddition of azomethine imines to 2-acryloyl-3-pyrazolidinone is described. The corresponding cycloadducts are isolated with high diastereoselectivities (up to >96:4 exo/endo) and enantioselectivities (up to 98% ee).
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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 ...
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Saturated five-membered nitrogen heterocycles, such as pyrrolidines, indolines, and isoxazolidines, appear as subunits in a broad array of biologically active and medicinally significant molecules [1]. As such, the synthesis of these compounds has been of longstanding interest. Many classical approaches to the construction of these heterocycles involve the use of C N bond-forming reactions such...
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ورودعنوان ژورنال:
- Journal of the American Chemical Society
دوره 125 36 شماره
صفحات -
تاریخ انتشار 2003