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

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journal contribution
posted on 21.08.1998 by Scott E. Denmark, Julie A. Dixon
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.

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