Stereochemical Studies of Chiral Acyclic Nitroxides Coupling with a Prochiral Radical

Abstract

A series of acyclic chiral nitroxides bearing a hydrogen atom on the carbon adjacent to the nitroxide nitrogen was investigated for stereoselectivity in a coupling reaction with the prochiral radical 1‐phenethyl. In one case, an x‐ray structure of the major diastereomer was obtained, which corroborates a model for predicting the stereoselectivity.

Keywords:

• Diastereoselectivity
• Prochiral radical
• Nitroxide
• N‐Alkoxyamine

Acknowledgments

Financial support from the National Science Foundation (CHE 9527647 and CHE 0078852) is gratefully acknowledged.

Notes

^aThe crystallographic data for 6a has been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC 205620. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: [phone]; e‐mail: [email protected]).