Tandem Inter [4 + 2]/Intra [3 + 2] Cycloadditions of Nitroalkenes. The Bridged Mode (β-Tether)

Autor:	Julie A. Dixon, Scott E. Denmark
Rok vydání:	1998
Předmět:	chemistry.chemical_compound chemistry Tandem Stereochemistry Yield (chemistry) Intramolecular force Organic Chemistry Nitro Nitroso Cycloaddition
Zdroj:	The Journal of Organic Chemistry. 63:6167-6177
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo9802168
Popis:	A new variation of the tandem inter [4 + 2]/intra [3 + 2] cycloaddition of nitroalkenes has been developed. This method involves the Lewis acid-promoted [4 + 2] cycloaddition of nitro olefins 12 with 1-alkoxy-1,4-dienes 3. The resulting nitronates 13, bearing a C(5) tethered dipolarophile, undergo thermal, intramolecular [3 + 2] cycloaddition to afford stable tricyclic nitroso acetals 14, which can be subsequently reduced to unveil a new carbocycle 16. Thus, in three steps, highly functionalized aminocyclopentanes can be stereoselectively constructed in high yield.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::8960a031d4c82f2f8960aa478d6098d5 https://doi.org/10.1021/jo9802168 Zobrazit plný text záznamu