Concepedia

Control of Enantioselectivity in the Photochemical Conversion of α-Oxoamides into β-Lactam Derivatives

Arunkumar Natarajan, Keyan Wang, V. Ramamurthy, John R. Scheffer, Brian O. Patrick

Organic Letters · 2002 · 89 citations · 23 references

DOI

Concepts

Abstract

[reaction: see text]. Several approaches to asymmetric induction in the alpha-oxoamide (1) to beta-lactam (2) photorearrangement are described. Best results are obtained via irradiation of ionic and covalent chiral auxiliary-containing reactants in the crystalline state and in the interior supercages of zeolites.

References

23

The Isoinversion Principle—a General Model of Chemical Selectivity

Helmut Buschmann, Hans‐Dieter Scharf, Norbert Hoffmann et al. · Angewandte Chemie International Edition in English · 1991 · 344 citations

, , +15

On the Stability of Amino Acid Zwitterions in the Gas Phase:  The Influence of Derivatization, Proton Affinity, and Alkali Ion Addition

Thomas Wyttenbach, Matthias Witt, Michael T. Bowers · Journal of the American Chemical Society · 2000 · 268 citations

, , +17

Structure of Cationized Arginine (Arg·M<sup>+</sup>, M = H, Li, Na, K, Rb, and Cs) in the Gas Phase:  Further Evidence for Zwitterionic Arginine

Rebecca A. Jockusch, William D. Price, Evan R. Williams · The Journal of Physical Chemistry A · 1999 · 182 citations

, , +17

Complexation of Na<sup>+</sup> and K<sup>+</sup> to Aromatic Amino Acids:  A Density Functional Computational Study of Cation-π Interactions

Robert C. Dunbar · The Journal of Physical Chemistry A · 2000 · 158 citations

, , +17

Effect of Metal Ion and Water Coordination on the Structure of a Gas-Phase Amino Acid

Rebecca A. Jockusch, Andrew Lemoff, Evan R. Williams · Journal of the American Chemical Society · 2001 · 152 citations

, , +17