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Synthesis of 1,2,3-trisubstituted pyrrolidines and 2,3-disubstituted tetrahydrofurans via diastereoselective reductive cyclization of γ-chloroimines and γ-chloroketones

Naga Venkata Sastry Mudiganti UGent, Sven Mangelinckx UGent, Bart Lucas UGent and Norbert De Kimpe UGent (2011) SYNLETT. p.2852-2856
abstract
A new diastereoselective synthetic approach towards 1,2,3-trisubstituted pyrrolidines and 2,3-disubstituted tetrahydrofurans is described. The synthesis of the pyrrolidines involves reductive cyclization of gamma-chloroketimines, which were generated in situ from the reaction of 3-substituted 5-chloro-2-pentanones and a primary amine. Various reduction conditions were explored to induce a diastereoselective reductive cyclization. 2,3-Disubstituted tetrahydrofurans were obtained by the direct reduction of 3-substituted 5-chloro-2-pentanones with sodium borohydride.
Please use this url to cite or link to this publication:
author
organization
alternative title
Synthesis of 1,2,3-trisubstituted pyrrolidines and 2,3-disubstituted tetrahydrofurans via diastereoselective reductive cyclization of gamma-chloroimines and gamma-chloroketones
year
type
journalArticle (original)
publication status
published
subject
keyword
pyrrolidines, tetrahydrofurans, SATURATED HETEROCYCLES, AZOMETHINE YLIDES, BETA, RING, CARBOETHERIFICATION, HETEROCYCLIC CHEMISTRY, CARBOAMINATION REACTIONS, STEREOSELECTIVE-SYNTHESIS, 3-HALO-1-AZAALLYLIC ANIONS, cyclization, haloimines, haloketones, HALOGENATED IMINO COMPOUNDS
journal title
SYNLETT
Synlett
issue
19
pages
2852 - 2856
Web of Science type
Article
Web of Science id
000297847700019
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
2.71 (2011)
JCR rank
18/56 (2011)
JCR quartile
2 (2011)
ISSN
0936-5214
DOI
10.1055/s-0031-1289544
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
1997573
handle
http://hdl.handle.net/1854/LU-1997573
date created
2012-01-19 20:56:59
date last changed
2012-02-09 15:25:56
@article{1997573,
  abstract     = {A new diastereoselective synthetic approach towards 1,2,3-trisubstituted pyrrolidines and 2,3-disubstituted tetrahydrofurans is described. The synthesis of the pyrrolidines involves reductive cyclization of gamma-chloroketimines, which were generated in situ from the reaction of 3-substituted 5-chloro-2-pentanones and a primary amine. Various reduction conditions were explored to induce a diastereoselective reductive cyclization. 2,3-Disubstituted tetrahydrofurans were obtained by the direct reduction of 3-substituted 5-chloro-2-pentanones with sodium borohydride.},
  author       = {Mudiganti, Naga Venkata Sastry and Mangelinckx, Sven and Lucas, Bart and De Kimpe, Norbert},
  issn         = {0936-5214},
  journal      = {SYNLETT},
  keyword      = {pyrrolidines,tetrahydrofurans,SATURATED HETEROCYCLES,AZOMETHINE YLIDES,BETA,RING,CARBOETHERIFICATION,HETEROCYCLIC CHEMISTRY,CARBOAMINATION REACTIONS,STEREOSELECTIVE-SYNTHESIS,3-HALO-1-AZAALLYLIC ANIONS,cyclization,haloimines,haloketones,HALOGENATED IMINO COMPOUNDS},
  language     = {eng},
  number       = {19},
  pages        = {2852--2856},
  title        = {Synthesis of 1,2,3-trisubstituted pyrrolidines and 2,3-disubstituted tetrahydrofurans via diastereoselective reductive cyclization of \ensuremath{\gamma}-chloroimines and \ensuremath{\gamma}-chloroketones},
  url          = {http://dx.doi.org/10.1055/s-0031-1289544},
  year         = {2011},
}

Chicago
Mudiganti, Naga Venkata Sastry, Sven Mangelinckx, Bart Lucas, and Norbert De Kimpe. 2011. “Synthesis of 1,2,3-trisubstituted Pyrrolidines and 2,3-disubstituted Tetrahydrofurans via Diastereoselective Reductive Cyclization of Γ-chloroimines and Γ-chloroketones.” Synlett (19): 2852–2856.
APA
Mudiganti, N. V. S., Mangelinckx, S., Lucas, B., & De Kimpe, N. (2011). Synthesis of 1,2,3-trisubstituted pyrrolidines and 2,3-disubstituted tetrahydrofurans via diastereoselective reductive cyclization of γ-chloroimines and γ-chloroketones. SYNLETT, (19), 2852–2856.
Vancouver
1.
Mudiganti NVS, Mangelinckx S, Lucas B, De Kimpe N. Synthesis of 1,2,3-trisubstituted pyrrolidines and 2,3-disubstituted tetrahydrofurans via diastereoselective reductive cyclization of γ-chloroimines and γ-chloroketones. SYNLETT. 2011;(19):2852–6.
MLA
Mudiganti, Naga Venkata Sastry, Sven Mangelinckx, Bart Lucas, et al. “Synthesis of 1,2,3-trisubstituted Pyrrolidines and 2,3-disubstituted Tetrahydrofurans via Diastereoselective Reductive Cyclization of Γ-chloroimines and Γ-chloroketones.” SYNLETT 19 (2011): 2852–2856. Print.