Conjugate Addition of Hydroxylamines, Oximes and Hydroxamic Acids
Published Online: 15 SEP 2010
Copyright © 2009 John Wiley & Sons, Ltd. All rights reserved.
Patai's Chemistry of Functional Groups
How to Cite
Du, Y., Mao, D., Zhang-Negrerie, D. and Zhao, K. 2010. Conjugate Addition of Hydroxylamines, Oximes and Hydroxamic Acids. Patai's Chemistry of Functional Groups.
- Published Online: 15 SEP 2010
- 1 General Introduction
- 2 Conjugate Addition of Hydroxylamine and Itsderivatives
- 3 Conjugate Addition of Oximes
- 4 Conjugate Addition of Hydroxamic Acids
- 5 Conclusions
- 6 Acknowledgments
The conjugate addition of hydroxylamines, oximes and hydroxamic acids provides convenient route to incorporate an NO moiety into various Michael acceptors. This chapter reviews comprehensive experimental reactions on the formation of carbonnitrogen and carbonoxygen bonds via conjugate addition of hydroxylamines, oximes and hydroxamic acids to alkenes, alkynes or allenes attached to one or more electron-withdrawing groups. Hydroxylamine derivatives predominantly undergo N-centered conjugate addition, while for the ambient nucleophilic oximes and hydroxamic acids, both N-centered and O-centered conjugate addition are operative by control of the reaction conditions. A concerted cycloaddition mechanism has been well established for the conjugate addition of N-substituted hydroxylamines. The last decade has witnessed enormous growth in enantioselective conjugate addition of hydroxylamine derivatives and the O-centered oximes.
Keywords: Conjugate addition, Hydroxylamines, Oximes, Hydroxamic acids, 1,4-Adducts, Michael acceptor, Concerted cycloaddition, Asymmetric conjugate addition, Nitrone