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Tandem addition of phosphite nucleophiles across unsaturated nitrogen-containing systems : mechanistic insights on regioselectivity

(2017) JOURNAL OF ORGANIC CHEMISTRY. 82(1). p.188-201
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Abstract
The addition of phosphite nucleophiles across linear unsaturated imines is a powerful and atom-economical methodology for the synthesis of aminophosphonates. These products are of interest from both a biological and a synthetic point of view: they act as amino acid transition state analogs and Horner-Wadsworth-Emmons reagents, respectively. In this work the reaction between dialkyl trimethylsilyl phosphites and alpha,beta,gamma,delta-diunsaturated imines was evaluated as a continuation of our previous efforts in the field. As such, the first conjugate 1,6-addition of a phosphite nucleophile across a linear unsaturated N-containing system is reported herein. Theoretical calculations were performed to rationalize the observed regioselectivites and to shed light on the proposed mechanism.
Keywords
CATALYZED ASYMMETRIC 1, 6-ADDITION, BOND FORMATION, ALPHA, BETA-UNSATURATED IMINES, THEORETICAL RATIONALIZATION, ORGANOPHOSPHORUS COMPOUNDS, CONJUGATE ADDITION, ACID ANALOGS, HIGHLY REGIO, P BOND, REAGENTS

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Chicago
Debrouwer, Wouter, Dietmar Hertsen, Thomas Heugebaert, Esma Birsen Boydas, Veronique Van Speybroeck, Saron Catak, and Christian Stevens. 2017. “Tandem Addition of Phosphite Nucleophiles Across Unsaturated Nitrogen-containing Systems : Mechanistic Insights on Regioselectivity.” Journal of Organic Chemistry 82 (1): 188–201.
APA
Debrouwer, W., Hertsen, D., Heugebaert, T., Boydas, E. B., Van Speybroeck, V., Catak, S., & Stevens, C. (2017). Tandem addition of phosphite nucleophiles across unsaturated nitrogen-containing systems : mechanistic insights on regioselectivity. JOURNAL OF ORGANIC CHEMISTRY, 82(1), 188–201.
Vancouver
1.
Debrouwer W, Hertsen D, Heugebaert T, Boydas EB, Van Speybroeck V, Catak S, et al. Tandem addition of phosphite nucleophiles across unsaturated nitrogen-containing systems : mechanistic insights on regioselectivity. JOURNAL OF ORGANIC CHEMISTRY. 2017;82(1):188–201.
MLA
Debrouwer, Wouter, Dietmar Hertsen, Thomas Heugebaert, et al. “Tandem Addition of Phosphite Nucleophiles Across Unsaturated Nitrogen-containing Systems : Mechanistic Insights on Regioselectivity.” JOURNAL OF ORGANIC CHEMISTRY 82.1 (2017): 188–201. Print.
@article{8504497,
  abstract     = {The addition of phosphite nucleophiles across linear unsaturated imines is a powerful and atom-economical methodology for the synthesis of aminophosphonates. These products are of interest from both a biological and a synthetic point of view: they act as amino acid transition state analogs and Horner-Wadsworth-Emmons reagents, respectively. In this work the reaction between dialkyl trimethylsilyl phosphites and alpha,beta,gamma,delta-diunsaturated imines was evaluated as a continuation of our previous efforts in the field. As such, the first conjugate 1,6-addition of a phosphite nucleophile across a linear unsaturated N-containing system is reported herein. Theoretical calculations were performed to rationalize the observed regioselectivites and to shed light on the proposed mechanism.},
  author       = {Debrouwer, Wouter and Hertsen, Dietmar and Heugebaert, Thomas and Boydas, Esma Birsen and Van Speybroeck, Veronique and Catak, Saron and Stevens, Christian},
  issn         = {0022-3263},
  journal      = {JOURNAL OF ORGANIC CHEMISTRY},
  keyword      = {CATALYZED ASYMMETRIC 1,6-ADDITION,BOND FORMATION,ALPHA,BETA-UNSATURATED IMINES,THEORETICAL RATIONALIZATION,ORGANOPHOSPHORUS COMPOUNDS,CONJUGATE ADDITION,ACID ANALOGS,HIGHLY REGIO,P BOND,REAGENTS},
  language     = {eng},
  number       = {1},
  pages        = {188--201},
  title        = {Tandem addition of phosphite nucleophiles across unsaturated nitrogen-containing systems : mechanistic insights on regioselectivity},
  url          = {http://dx.doi.org/10.1021/acs.joc.6b02340},
  volume       = {82},
  year         = {2017},
}

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