Catalytic, Asymmetric Inverse Electron Demand Hetero Diels-Alder Reactions of o-Benzoquinone Derivatives and Ketene Enolates

Authors

  • Daniel H. Paull
  • Jamison Wolfer
  • James W. Grebinski
  • Anthony Weatherwax
  • Thomas Lectka

DOI:

https://doi.org/10.2533/chimia.2007.240

Keywords:

Asymmetric catalysis, Bifunctional catalysis, [4 2] cycloaddition, Hetero diels-alder, Ketene enolates

Abstract

We present an array of [4+2] cycloaddition reactions between ketene enolates, catalytically derived from acid chlorides and cinchona alkaloid nucleophilic catalysts in the presence of stoichiometric base, and o-benzoquinone derivatives. These cycloaddition reactions proceed with excellent stereochemical control (up to >99% ee). In fact, for both the o-benzoquinone imide and the o-benzoquinone diimide manifolds, these Diels-Alder reactions occurred with uniformly >99% ee. The wide scope of this methodology provides access to a diverse range of biologically and synthetically useful chiral products, including ?-hydroxyesters, non-natural ?-amino acids, quinoxalinones, and many others, all with remarkable, catalytic control of regio- and stereochemistry.

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Published

2007-05-30

How to Cite

[1]
D. H. Paull, J. Wolfer, J. W. Grebinski, A. Weatherwax, T. Lectka, Chimia 2007, 61, 240, DOI: 10.2533/chimia.2007.240.

Issue

Section

Scientific Articles