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

Wouter Debrouwer, Dietmar Hertsen UGent, Thomas Heugebaert UGent, Esma Birsen Boydas, Veronique Van Speybroeck UGent, Saron Catak UGent and Christian Stevens UGent (2017) JOURNAL OF ORGANIC CHEMISTRY. 82(1). p.188-201
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.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
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
journal title
JOURNAL OF ORGANIC CHEMISTRY
J. Org. Chem.
volume
82
issue
1
pages
188 - 201
Web of Science type
Article
Web of Science id
000391781900019
ISSN
0022-3263
DOI
10.1021/acs.joc.6b02340
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
8504497
handle
http://hdl.handle.net/1854/LU-8504497
date created
2017-01-25 19:05:13
date last changed
2017-12-05 13:02:43
@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},
}

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.