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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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MLA
Debrouwer, Wouter 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.
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.
Chicago author-date
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.
Chicago author-date (all authors)
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.
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.
IEEE
[1]
W. Debrouwer et al., “Tandem addition of phosphite nucleophiles across unsaturated nitrogen-containing systems : mechanistic insights on regioselectivity,” JOURNAL OF ORGANIC CHEMISTRY, vol. 82, no. 1, pp. 188–201, 2017.
@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},
  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},
  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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