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Kinetic Resolution of Aminoalkenes by Asymmetric Hydroamination: A Mechanistic Study by Alexander L. Reznichenko; Frank Hampel; Kai C. Hultzsch is a Chemistry article available to read on EtoBox.

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## Abstract The kinetic resolution of chiral aminoalkenes by hydroamination–cyclization was studied by using 3,3′‐bis(triarylsilyl)‐substituted binaphtholate rare‐earth‐metal complexes. The resolution of 1‐arylaminopentenes proceeds with high efficiency and high __trans__‐diastereoselectivity, whereas the resolution process of 1‐alkylaminopentenes suffers from decreasing resolution efficiency with increasing steric demand of the aliphatic substituent. Kinetic studies of the matching and mismatching substrate–catalyst pair by using enantiopure substrates and either the (__R__)‐ or (__S__)‐binaphtholate catalysts revealed that the difference in resolution efficiency stems from a shift of the Curtin–Hammett pre‐equilibrium. Although 1‐arylaminopentenes favor the matching substrate–catalyst complex, preference for the mismatching substrate–catalyst complex for 1‐alkylaminopentenes diminishes resolution efficiency. Nevertheless, the relative cyclization rate for the two diastereomeric substrate–catalyst complexes remains in a typical range of 7–10:1. Plausible attractive π interactions between the aryl substituent and either the metal center or the aromatic system of the bis(triarylsily

Who reads Kinetic Resolution of Aminoalkenes by Asymmetric Hydroamination: A Mechanistic Study?

Author

Alexander L. Reznichenko; Frank Hampel; Kai C. Hultzsch

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Ltd.; Wiley (ISSN 0947-6539)

Published

2009

Language

EN

Field

Chemistry (Physical Sciences)