Concepedia

Pseudoephedrine as a Chiral Auxiliary for Asymmetric Michael Reactions:  Synthesis of 3-Aryl-δ-lactones

Jacqueline H. Smitrovich, Geneviève N. Boice, Chuanxing Qu, Lisa DiMichele, Todd D. Nelson, Mark A. Huffman, Jerry A. Murry, James M. McNamara, Paul J. Reider

Organic Letters · 2002 · 39 citations · 11 references

DOI

Concepts

Abstract

[reaction: see text] The asymmetric Michael reaction of pseudoephedrine amides is reported. The 1,5-dicarbonyl products are converted to 3-aryl-delta-lactones in a two-step reduction/lactonization sequence. This method provides access to enantiomerically enriched trans-3,4-disubstituted delta-lactones.

References

11

Enantioselective Michael Addition of Nitromethane to α,β-Enones Catalyzed by Chiral Quaternary Ammonium Salts. A Simple Synthesis of (<i>R</i>)-Baclofen

E. J. Corey, Fuyao Zhang · Organic Letters · 2000 · 219 citations

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Acyclic stereoselection. 47. Stereochemistry of the Michael addition of ester and ketone enolates to .alpha.,.beta.-unsaturated ketones

D. A. OARE, Clayton H. Heathcock · The Journal of Organic Chemistry · 1990 · 120 citations

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Greatly Simplified Procedures for the Synthesis of α-Amino Acids by the Direct Alkylation of Pseudoephedrine Glycinamide Hydrate

Andrew G. Myers, Patrick Schnider, Soojin Kwon et al. · The Journal of Organic Chemistry · 1999 · 75 citations

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New polymer-supported catalysts derived from Cinchona alkaloids: Their use in the asymmetric Michael reaction

Rosana Álvarez, Marie‐Agnes Hourdin, Christian Cavé et al. · Tetrahedron Letters · 1999 · 60 citations

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Progress toward the Total Synthesis of Callipeltin A (I):  Asymmetric Synthesis of (3<i>S</i>,4<i>R</i>)-3,4-Dimethylglutamine

Bo Liang, Patrick J. Carroll, Madeleine M. Joullié · Organic Letters · 2000 · 58 citations

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