Facile synthesis of 7-dimethylamino-endo-tricyclo[5.2.2.01,6]-undec-10-en-9-ones

Yao Ting Wu, Heiko Schirmer, Mathias Noltemeyer, Armin De Meijere

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Pentacarbonyl[(2E)-3-cyclohexenyl-3-dimethylamino-1-ethoxy-2-propen-1- ylidene]chromium (2) yields 7-dimethylamino-endo-tricyclo[5.2.2.01,6]undec-10-en-9-ones 5 (15-88%, 12 examples) upon treatment with alkynes 3 in pyridine, most probably by a 6π-electrocyclization followed by a subsequent reductive elimination/intermolecular Diels-Alder reaction with the alkyne and eventual hydrolysis. The direct cyclization of 2 to the cyclohexane-annelated cyclopentadiene 6 is faster than the usual alkyne insertion of α,β-unsaturated Fischer carbene complexes. The [4+2] cycloadditions of 7 and the added alkynes 3 occur with high degrees of regio- and complete diastereoselectivity.

Original languageEnglish
Pages (from-to)2501-2506
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number13
DOIs
Publication statusPublished - 2001 Jul

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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