Direct enantioselective synthesis of bicyclic Diels-Alder products

Henrik Sundén, Ramon Rios, Yongmei Xu, Lars Eriksson, Armando Córdova

Research output: Contribution to journalArticlepeer-review

53 Scopus citations

Abstract

The direct amine-catalyzed enantioselective Diels-Alder reaction between α,β-unsaturated cyclic ketones and nitroolefins is presented. A simple diamine catalyzes the asymmetric Diels-Alder reaction with high stereoselectivity and furnishes the corresponding Diels-Alder adducts in good to high yields with >25:1 dr and up to 86% ee. The study demonstrates a convenient entry to functionalized bicyclic molecules contaning four stereocenters that are formed with excellent diastreoselectivity and good to high enantioselectivity.

Original languageBritish English
Pages (from-to)2549-2555
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume349
Issue number17-18
DOIs
StatePublished - Dec 2007

Keywords

  • α,β-unsaturated cyclic ketones
  • Asymmetric catalysis
  • Diels-Alder reaction
  • Nitroolefins
  • Organocatalysis

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