Concepedia

N‐Heterocyclic Carbene‐Catalyzed Enantioselective Annulation of Bromoenal and 1,3‐Dicarbonyl Compounds

Fang‐Gang Sun, Li‐Hui Sun, Song Ye

Advanced Synthesis & Catalysis · 2011 · 202 citations · 78 references

DOI

Concepts

Abstract

Abstract Highly enantioselective [3+3] annulation reactions of bromoenals and 1,3‐dicarbonyl compounds are reported. In addition, both enantiomers of the resultant dihydropyranone could be easily obtained by choosing N‐heterocyclic carbenes (NHCs) with the same stereocenter but different substituents under the optimized reaction conditions.

References

78

On the Mechanism of Thiamine Action. IV.<sup>1</sup> Evidence from Studies on Model Systems

Ronald Breslow · Journal of the American Chemical Society · 1958 · 1.7K citations

, , +5

Organocatalyzed Conjugate Umpolung of α,β‐Unsaturated Aldehydes for the Synthesis of γ‐Butyrolactones

Christian Burstein, Frank Glorius · Angewandte Chemie International Edition · 2004 · 722 citations

, , +5

<i>N</i>-Heterocyclic Carbene-Catalyzed Generation of Homoenolates:  γ-Butyrolactones by Direct Annulations of Enals and Aldehydes

Stephanie S. Sohn, E.L. Rosen, Jeffrey W. Bode · Journal of the American Chemical Society · 2004 · 701 citations

, , +16

Highly Enantioselective Azadiene Diels−Alder Reactions Catalyzed by Chiral N-Heterocyclic Carbenes

Ming He, Justin R. Struble, Jeffrey W. Bode · Journal of the American Chemical Society · 2006 · 579 citations

, , +14

A Highly Enantioselective Catalytic Intramolecular Stetter Reaction

Mark S. Kerr, Javier Read de Alaniz, Tomislav Rovis · Journal of the American Chemical Society · 2002 · 498 citations

, , +12