Tandem double intramolecular [4+2]/[3+2] cycloadditions of nitroalkenes. The fused/bridged mode

Scott E. Denmark, Laurent Gomez

Research output: Contribution to journalArticlepeer-review

Abstract

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)8015-8024
Number of pages10
JournalJournal of Organic Chemistry
Volume68
Issue number21
DOIs
StatePublished - Oct 17 2003

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Tandem double intramolecular [4+2]/[3+2] cycloadditions of nitroalkenes. The fused/bridged mode'. Together they form a unique fingerprint.

Cite this