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Direct regio- and diastereoselective diphosphonylation of cyclic enamines : one-pot synthesis of α,α′-bis(diphenylphosphoryl)- and α,α′-bis(diphenylphosphorothioyl)cycloalkanones

Nejib Jebli, Wouter Debrouwer, Jan Berton UGent, Kristof Van Hecke UGent, Christian Stevens UGent and Soufiane Touil (2017) SYNLETT. 28(10). p.1160-1164
abstract
A straightforward regio- and diastereoselective process has been developed for the synthesis of unprecedented symmetrical trans-alpha,alpha '-bis(diphenylphosphoryl)- and alpha,alpha '-bis(diphenylphosphorothioyl)cycloalkanones, through the reaction of cyclic enamines with excess P-chlorodiphenylphosphine in the presence of triethylamine, followed by oxidation or sulfurization and hydrolytic workup.
Please use this url to cite or link to this publication:
author
organization
alternative title
Direct regio- and diastereoselective diphosphonylation of cyclic enamines : one-pot synthesis of alpha,alpha ′-bis(diphenylphosphoryl)- and alpha,alpha ′-bis(diphenylphosphorothioyl)cycloalkanones
year
type
journalArticle (original)
publication status
published
subject
keyword
enamines, P-chlorodiphenylphosphine, alpha, alpha '-bis(diphenylphosphoryl)cycloalkanones, alpha, alpha '-bis(diphenylphosphorothioyl)cycloalkanones, P-ligands, PHOSPHINE-OXIDE, TRIISOBUTYLPHOSPHINE SULFIDE, BETA-KETOPHOSPHONATES, EXTRACTANT PROPERTIES, LANTHANIDE COMPLEXES, LIGAND, ACID, DERIVATIVES, KETONES, IMINES
journal title
SYNLETT
Synlett
volume
28
issue
10
pages
1160 - 1164
Web of Science type
Article
Web of Science id
000402750500005
ISSN
0936-5214
1437-2096
DOI
10.1055/s-0036-1588970
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
8545187
handle
http://hdl.handle.net/1854/LU-8545187
date created
2018-01-16 15:26:10
date last changed
2018-07-02 22:30:10
@article{8545187,
  abstract     = {A straightforward regio- and diastereoselective process has been developed for the synthesis of unprecedented symmetrical trans-alpha,alpha '-bis(diphenylphosphoryl)- and alpha,alpha '-bis(diphenylphosphorothioyl)cycloalkanones, through the reaction of cyclic enamines with excess P-chlorodiphenylphosphine in the presence of triethylamine, followed by oxidation or sulfurization and hydrolytic workup.},
  author       = {Jebli, Nejib and Debrouwer, Wouter and Berton, Jan and Van Hecke, Kristof and Stevens, Christian and Touil, Soufiane},
  issn         = {0936-5214},
  journal      = {SYNLETT},
  keyword      = {enamines,P-chlorodiphenylphosphine,alpha,alpha '-bis(diphenylphosphoryl)cycloalkanones,alpha,alpha '-bis(diphenylphosphorothioyl)cycloalkanones,P-ligands,PHOSPHINE-OXIDE,TRIISOBUTYLPHOSPHINE SULFIDE,BETA-KETOPHOSPHONATES,EXTRACTANT PROPERTIES,LANTHANIDE COMPLEXES,LIGAND,ACID,DERIVATIVES,KETONES,IMINES},
  language     = {eng},
  number       = {10},
  pages        = {1160--1164},
  title        = {Direct regio- and diastereoselective diphosphonylation of cyclic enamines : one-pot synthesis of \ensuremath{\alpha},\ensuremath{\alpha}{\textquotesingle}-bis(diphenylphosphoryl)- and \ensuremath{\alpha},\ensuremath{\alpha}{\textquotesingle}-bis(diphenylphosphorothioyl)cycloalkanones},
  url          = {http://dx.doi.org/10.1055/s-0036-1588970},
  volume       = {28},
  year         = {2017},
}

Chicago
Jebli, Nejib, Wouter Debrouwer, Jan Berton, Kristof Van Hecke, Christian Stevens, and Soufiane Touil. 2017. “Direct Regio- and Diastereoselective Diphosphonylation of Cyclic Enamines : One-pot Synthesis of Α,α′-bis(diphenylphosphoryl)- and Α,α′-bis(diphenylphosphorothioyl)cycloalkanones.” Synlett 28 (10): 1160–1164.
APA
Jebli, N., Debrouwer, W., Berton, J., Van Hecke, K., Stevens, C., & Touil, S. (2017). Direct regio- and diastereoselective diphosphonylation of cyclic enamines : one-pot synthesis of α,α′-bis(diphenylphosphoryl)- and α,α′-bis(diphenylphosphorothioyl)cycloalkanones. SYNLETT, 28(10), 1160–1164.
Vancouver
1.
Jebli N, Debrouwer W, Berton J, Van Hecke K, Stevens C, Touil S. Direct regio- and diastereoselective diphosphonylation of cyclic enamines : one-pot synthesis of α,α′-bis(diphenylphosphoryl)- and α,α′-bis(diphenylphosphorothioyl)cycloalkanones. SYNLETT. 2017;28(10):1160–4.
MLA
Jebli, Nejib, Wouter Debrouwer, Jan Berton, et al. “Direct Regio- and Diastereoselective Diphosphonylation of Cyclic Enamines : One-pot Synthesis of Α,α′-bis(diphenylphosphoryl)- and Α,α′-bis(diphenylphosphorothioyl)cycloalkanones.” SYNLETT 28.10 (2017): 1160–1164. Print.