Intramolecular [4 + 2] cycloaddition of nitroalkenes for construction of vicinal quaternary stereocenters

Scott E Denmark, Ramil Y. Baiazitov

Research output: Contribution to journalArticle

Abstract

(Chemical Equation Presented) Nitroalkene (E)-1 has been synthesized to test the feasibility of an intramolecular [4 + 2] cycloaddition in a planned synthesis of daphnilactone B. This nitro olefin contains two unique structural features, a nitromethylene lactone and a pendant diene, that combine under the action of SnCl4 in a highly selective fashion to afford nitronates 2a and 2b. These products represent the correct relationship for the vicinal quaternary stereogenic centers in the core of daphnilactone B.

Original languageEnglish (US)
Pages (from-to)5617-5620
Number of pages4
JournalOrganic Letters
Volume7
Issue number25
DOIs
StatePublished - Dec 8 2005

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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