A Palladium-Catalyzed Vinylcyclopropane (3 + 2) Cycloaddition Approach to the Melodinus Alkaloids
نویسندگان
چکیده
منابع مشابه
A palladium-catalyzed vinylcyclopropane (3+2) cycloaddition approach to the Melodinus alkaloids.
A palladium-catalyzed (3+2) cycloaddition of a vinylcyclopropane and a β-nitrostyrene is employed to rapidly assemble the cyclopentane core of the Melodinus alkaloids. The ABCD ring system of the natural product family is prepared in six steps from commercially available materials.
متن کاملPalladium-catalyzed [3 + 2] intramolecular cycloaddition of alk-5-enylidenecyclopropanes.
Readily accessible alk-5-enylidenecyclopropanes undergo [3 + 2] intramolecular cycloaddition reactions upon treatment with appropriate palladium complexes. The method allows the rapid and efficient assembly of a variety of bicyclo[3.3.0]octane systems with up to three stereocenters. Preliminary theoretical calculations uncovered previously unsuspected mechanistic possibilities based on either a...
متن کاملHighly functionalized donor-acceptor cyclopropanes applied toward the synthesis of the Melodinus alkaloids.
A series of highly substituted vinylcyclopropanes were prepared and examined as reaction partners in a palladium-catalyzed (3 + 2) cycloaddition with nitrostyrenes. Described herein are our efforts to synthesize an elusive 1,1-divinylcyclopropane by several distinct approaches, and to apply surrogates of this fragment toward the synthesis of the Melodinus alkaloids.
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...
متن کاملChiral bifunctional ferrocenylphosphine catalyzed highly enantioselective [3 + 2] cycloaddition reaction.
A series of air-stable ferrocenylphosphines LB1-LB8 were designed and prepared in high yields. (R,SFc)-ferrocenylphosphine LB5 was found to efficiently promote the asymmetric [3 + 2] cycloaddition of Morita-Baylis-Hillman carbonates with maleimides to afford the corresponding bicyclic imides with 84-99% ee and 67-99% yield. Interestingly, the configuration of these products was contrary to thos...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: Organic Letters
سال: 2011
ISSN: 1523-7060,1523-7052
DOI: 10.1021/ol2017615