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Enantioselective Staudinger Synthesis of β-Lactams Catalyzed by a Planar-Chiral Nucleophile1
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Abstract
The development of efficient methods for the stereoselective generation of β-lactams is an important goal, due to their biological activity and their utility as synthetic intermediates. The Staudinger reaction, an overall [2 + 2] cycloaddition of a ketene with an imine, provides a nicely convergent route to this family of compounds. Nearly all studies to date of asymmetric variants of the Staudinger reaction have focused on the use of chiral auxiliaries to control the stereochemistry of the β-lactam. In this report, we establish that a planar-chiral derivative of 4-(pyrrolidino)pyridine serves as a very effective enantioselective catalyst for the Staudinger β-lactam synthesis, coupling a range of symmetrical and unsymmetrical ketenes with an array of imines with very good stereoselection and yield.
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This article has been cited by 44 ACS Journal articles (5 most recent appear below).
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Josiphos-Catalyzed Asymmetric Homodimerization of Ketoketenes
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Ahmad A. Ibrahim, Pei-Hsun Wei, Gero D. Harzmann, and Nessan J. KerriganThe Journal of Organic Chemistry2010 75 (22), 7901-7904In this paper the development of a chiral phosphine-catalyzed homodimerization of ketoketenes that provides access to a variety of highly substituted ketoketene dimer β-lactones (11 examples) is reported. The Josiphos catalytic system displays good to ...
Stereoselective Synthesis of Chiral 4-(1-Chloroalkyl)-β-Lactams Starting from Amino Acids and Their Transformation into Functionalized Chiral Azetidines and Pyrrolidines
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Stijn Dekeukeleire, Matthias D’hooghe, Karl W. Törnroos and Norbert De KimpeThe Journal of Organic Chemistry2010 75 (17), 5934-5940Chiral short-chain α-chloroaldehydes were prepared starting from enantiomerically pure amino acids in a three-step approach, thus providing a practical synthetic alternative for known organocatalytic α-chlorination procedures. The latter aldehydes proved ...
Unexpected Inversions in Asymmetric Reactions: Reactions with Chiral Metal Complexes, Chiral Organocatalysts, and Heterogeneous Chiral Catalysts
Mihály BartókChemical Reviews2010 110 (3), 1663-1705Unexpected Inversions in Asymmetric Reactions: Reactions with Chiral Metal Complexes, Chiral Organocatalysts, and Heterogeneous Chiral Catalysts
Mihály BartókChemical Reviews2010 110 (3), 1663-1705
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History
- Published In Issue February 27, 2002
- Received October 25, 2001
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