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Robinson DE, Holladay MW. Convenient preparation of O-linked polymer-bound N-substituted hydroxylamines, intermediates for synthesis of N-substituted hydroxamic acids. Org Lett. 2000;2(18):2777-9doi: 10.1021/ol006152g.
Robinson, D. E., & Holladay, M. W. (2000). Convenient preparation of O-linked polymer-bound N-substituted hydroxylamines, intermediates for synthesis of N-substituted hydroxamic acids. Organic letters, 2(18), 2777-9. https://doi.org/10.1021/ol006152g
Robinson, D E, and Holladay, M W. "Convenient preparation of O-linked polymer-bound N-substituted hydroxylamines, intermediates for synthesis of N-substituted hydroxamic acids." Organic letters vol. 2,18 (2000): 2777-9. doi: https://doi.org/10.1021/ol006152g
Robinson DE, Holladay MW. Convenient preparation of O-linked polymer-bound N-substituted hydroxylamines, intermediates for synthesis of N-substituted hydroxamic acids. Org Lett. 2000 Sep 07;2(18):2777-9. doi: 10.1021/ol006152g. PMID: 10964363.
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Org Lett. 2000 Sep 07;2(18):2777-9. doi: 10.1021/ol006152g.

Convenient preparation of O-linked polymer-bound N-substituted hydroxylamines, intermediates for synthesis of N-substituted hydroxamic acids.

Organic letters

D E Robinson, M W Holladay

Affiliations

  1. SIDDCO, Inc., 9040 S. Rita Road, Suite 2338, Tucson, Arizona 85747, USA.

PMID: 10964363 DOI: 10.1021/ol006152g

Abstract

[reaction: see text] An efficient procedure for preparation of O-linked polymer-bound N-substituted hydroxylamines by reduction of resin-bound oximes with borane.pyridine complex in the presence of dichloroacetic acid is reported. Other reducing systems commonly used for imine or oxime reduction were ineffective, including borane.pyridine in the presence of acetic acid. Oximes derived from a variety of aromatic and aliphatic aldehydes and ketones were successfully reduced. The N-substituted products were acylated and cleaved from resin to afford N-substituted hydroxamic acids.

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