Tandem double intramolecular [4 + 2]/[3 + 2] cycloadditions of nitroalkenes

Scott E. Denmark, Ramil Y. Baiazitov, Son T. Nguyen

Research output: Contribution to journalArticle

Abstract

(equation presented) A new class of tandem [4 + 2]/[3 + 2] cycloadditions of nitroalkenes is described in which both pericyclic processes are intramolecular. Two subclasses of intra [4 + 2]/intra [3 + 2] cycloadditions have been explored in which the dipolarophile is tethered at either C(5) or C(6) of the nitronate. For both families of precursors, the cycloadditions occur in good yield and are found to be highly regio-and stereoselective. This method converts linear polyenes to functionalized polycyclic systems bearing up to six stereogenic centers.

Original languageEnglish (US)
Pages (from-to)2907-2910
Number of pages4
JournalOrganic Letters
Volume3
Issue number18
DOIs
StatePublished - 2001

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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