Kinetic Isotope Effects in Asymmetric Reactions

被引：74

作者：

Giagou, Thomas ^{[1
]}

Meyer, Matthew P. ^{[1
]}

机构：

[1] Univ Calif Merced, Sch Nat Sci, Merced, CA 95344 USA

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 35期

关键词：

asymmetric reactions; kinetic isotope effects; reaction mechanisms; stereoselection; steric hindrance; EXPERIMENTAL TRANSITION-STATE; 1,3-ASYMMETRIC INDUCTION; FREQUENCY-SHIFTS; ALDOL REACTIONS; OPEN-CHAIN; HYDROGEN; MECHANISM; REDUCTION; PROLINE; STEREOCHEMISTRY;

D O I：

10.1002/chem.201001018

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Kinetic isotope effects are exquisitely sensitive probes of transition structure. As such, kinetic isotope effects offer a uniquely useful probe for the symmetry-breaking process that is inherent to stereoselective reactions. In this Concept article, we explore the role of steric and electronic effects in stereocontrol, and we relate these concepts to recent studies carried out in our laboratory. We also explore the way in which kinetic isotope effects serve as useful points of contact with computational models of transition structures. Finally, we discuss future opportunities for kinetic isotope effects to play a role in asymmetric catalyst development.

引用

页码：10616 / 10628

页数：13

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