Intramolecular Cycloaddition/Rearrangement of Alkylidenecyclopropane Nitrones from Palladium(0)-Catalyzed Alkylation of Amino Acid Derivatives
✍ Scribed by Marco Ferrara; Franca M. Cordero; Andrea Goti; Alberto Brandi; Karine Estieu; Renée Paugam; Jean Ollivier; Jacques Salaün
- Publisher
- John Wiley and Sons
- Year
- 1999
- Tongue
- English
- Weight
- 476 KB
- Volume
- 1999
- Category
- Article
- ISSN
- 1434-193X
No coin nor oath required. For personal study only.
✦ Synopsis
Several alkylidenecyclopropanes have been synthesized in moderate with most substituted substrates, but complete with phenylglycine and proline derivatives. The spirocyclopropane high yields and optical purity by palladium(0)-catalyzed substitution of 1-tosyloxy-1-vinyl cyclopropane using N-isoxazolidines were transformed by selective thermal rearrangements in octahydro-2H-pyrrolo[3,4-b]pyridin-7-ones tosylamino esters or glycolic ester as nucleophiles. The new alkylidenecyclopropanes were transformed to the and octahydrofuro [3,4-b]pyridin-7-one, uncommon ring systems resembling biologically active natural and nonnatural corresponding nitrones without loss of optical purity, except in the case of the phenylglycine derivative. The products. An example of the extension of the process to an alkylidenecyclopropane nitrile oxide is also reported. alkylidenecyclopropane nitrones underwent smooth in situ intramolecular cycloaddition with a stereoselectivity that was stereoselectivity. [3] It also fulfills the requirements of "atom in the presence of Pd 0 , [8] regioselective Pd 0 -catalyzed [3 ϩ Fax: (internat.) ϩ39-055-2476964 2] cycloaddition with olefinic and acetylenic substrates, [5] [9