Campus Units

Chemistry, Ames Laboratory

Document Type

Article

Publication Version

Published Version

Publication Date

10-12-2011

Journal or Book Title

ACS Catalysis

Volume

1

Issue

11

First Page

1637

Last Page

1642

DOI

10.1021/cs200511z

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.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

Included in

Chemistry Commons

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