Tandem inter [4 + 2]/intra [3 + 2] cycloadditions of nitroalkenes. Asymmetric synthesis of highly functionalized aminocyclopentanes using the bridged mode (β-tether) process

Scott E Denmark, Julie A. Dixon

Research output: Contribution to journalArticlepeer-review

Abstract

An asymmetric, tandem inter [4 + 2]/intra [3 + 2] bridged mode (β- tether) cycloaddition nitroalkenes has been developed. This new sequence involves the Lewis acid-promoted [4 + 2] cycloaddition of nitro olefins with enantiopure 1-alkoxy-1,4-dienes. The resulting nitronates, bearing a C(5) tethered dipolarophile, undergo thermal, intramolecular [3 + 2] cycloaddition to afford stable tricyclic nitroso acetals, which can be subsequently reduced to provide interesting aminocyclopentanes. Thus, in three steps, highly functionalized, enantiomerically enriched aminocyclopentanes can be constructed with good yield and high ee. Additionally, the Lewis acid was found to impart a remarkable influence on the stereochemical outcome of the [4 + 2] cycloaddition.

Original languageEnglish (US)
Pages (from-to)6178-6195
Number of pages18
JournalJournal of Organic Chemistry
Volume63
Issue number18
DOIs
StatePublished - Sep 4 1998

ASJC Scopus subject areas

  • Organic Chemistry

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