Prev. Article Next Article Table of Contents

Letter

[AlCl₃ + 2THF]: A New and Efficient Catalytic System for Diels−Alder Cycloaddition of α,β-Unsaturated Carbonyl Compounds under Solvent-Free Conditions

Supporting Info

Francesco Fringuelli,* Rugiada Girotti, Ferdinando Pizzo,* and Luigi Vaccaro;

CEMIN, Centro di Eccellenza Materiali Innovativi Nanostrutturati, Dipartimento di Chimica, Universit di Perugia, Via Elce di Sotto 8, I-06123 Perugia, Italy

Org. Lett., 2006, 8 (12), pp 2487–2489

DOI: 10.1021/ol060569q

Publication Date (Web): May 19, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, frifra@unipg.it, ; , pizzo@unipg.it

Abstract

[AlCl₃ + 2THF] is a new catalytic system for the Diels−Alder cycloaddition under SFC and air atmosphere. By using equimolar amounts of reactants, this catalyst prevents the polymerization of the diene and allows the corresponding adducts to be isolated with high regio- and stereocontrol and in excellent yields.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue June 08, 2006
Received March 8, 2006

Recommend & Share

Related Content

Chiral Oxazaborolidine−Aluminum Bromide Complexes Are Unusually Powerful and Effective Catalysts for Enantioselective Diels−Alder ReactionsJournal of the American Chemical Society
- Chiral Oxazaborolidine−Aluminum Bromide Complexes Are Unusually Powerful and Effective Catalysts for Enantioselective Diels−Alder Reactions
  Duan Liu, Eda Canales, and E. J. Corey
  Journal of the American Chemical Society 2007 129 (6), pp 1498–1499
  Abstract: Treatment of the chiral oxazaborolidine 1 with AlBr₃ generates the 1:1 complex 3, which is an even more potent Lewis acid catalyst than protonated 1 (i.e., 2) for enantioselective Diels−Alder reactions. Only 4 mol % of catalyst 3 is required to achieve ...
  Abstract | Full Text HTML | Hi-Res PDF
Asymmetric Diels−Alder Reactions Catalyzed by a Triflic Acid Activated Chiral OxazaborolidineJournal of the American Chemical Society
- Asymmetric Diels−Alder Reactions Catalyzed by a Triflic Acid Activated Chiral Oxazaborolidine
  E. J. Corey, Takanori Shibata, and Thomas W. Lee
  Journal of the American Chemical Society 2002 124 (15), pp 3808–3809
  Abstract: This paper reports a new method for the generation of chiral Lewis superacids by protonation of a non-Lewis acidic oxazaborolidine (1) with triflic acid. The resulting cationic species (3) are powerful and highly enantioselective catalysts for the Diels−...
  Abstract | Full Text HTML | Hi-Res PDF
Design of Chiral N-Triflyl Phosphoramide as a Strong Chiral Brønsted Acid and Its Application to Asymmetric Diels−Alder ReactionJournal of the American Chemical Society
- Design of Chiral N-Triflyl Phosphoramide as a Strong Chiral Brønsted Acid and Its Application to Asymmetric Diels−Alder Reaction
  Daisuke Nakashima and Hisashi Yamamoto
  Journal of the American Chemical Society 2006 128 (30), pp 9626–9627
  Abstract: A highly reactive and acidic chiral Brønsted acid catalyst, chiral N-triflyl phosphoramide, was developed. Highly enantioselective Diels−Alder reaction of α,β-unsaturated ketone with silyloxydiene was demonstrated using this chiral Brønsted acid catalyst. ...
  Abstract | Full Text HTML | Hi-Res PDF

Letter

[AlCl₃ + 2THF]: A New and Efficient Catalytic System for Diels−Alder Cycloaddition of α,β-Unsaturated Carbonyl Compounds under Solvent-Free Conditions