Concerted C–N/C–H Bond Formation in Highly Enantioselective Yttrium(III)-Catalyzed Hydroamination
Date
Authors
Major Professor
Advisor
Committee Member
Journal Title
Journal ISSN
Volume Title
Publisher
Authors
Research Projects
Organizational Units
Ames National Laboratory is a government-owned, contractor-operated national laboratory of the U.S. Department of Energy (DOE), operated by and located on the campus of Iowa State University in Ames, Iowa.
For more than 70 years, the Ames National Laboratory has successfully partnered with Iowa State University, and is unique among the 17 DOE laboratories in that it is physically located on the campus of a major research university. Many of the scientists and administrators at the Laboratory also hold faculty positions at the University and the Laboratory has access to both undergraduate and graduate student talent.
The Department of Chemistry seeks to provide students with a foundation in the fundamentals and application of chemical theories and processes of the lab. Thus prepared they me pursue careers as teachers, industry supervisors, or research chemists in a variety of domains (governmental, academic, etc).
History
The Department of Chemistry was founded in 1880.
Dates of Existence
1880-present
Related Units
- College of Liberal Arts and Sciences (parent college)
Journal Issue
Is Version Of
Versions
Series
Department
Abstract
A highly active oxazolinylborato yttrium hydroamination catalyst provides 2-methyl-pyrrolidines with excellent optical purities. The proposed mechanism, in which a yttrium(amidoalkene)amine complex reacts by concerted C–N and C–H bond formation, is supported by the rate law for conversion, substrate saturation under initial rates conditions, kinetic isotope effects, and isotopic perturbation of enantioselectivity. These features are conserved between oxazolinylborato Mg-, Y-, and Zr-mediated aminoalkene cyclizations, suggesting related transition states for all three systems. However, inversion of the products’ absolute configuration between yttrium and zirconium catalysts coordinated by the same 4S-oxazolinylborate ligands highlight dissimilar mechanisms of stereoinduction.
Comments
Reprinted (adapted) with permission from ACS Catalysis 1 (2011): 1637, doi: 10.1021/cs200511z. Copyright 2011 American Chemical Society.