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Asymmetric synthesis of chiral N-sulfinyl 3-alkyl- and 3-arylpiperidines by alpha-Alkylation of N-sulfinyl imidates with 1-Chloro-3-iodopropane

Filip Colpaert UGent, Sven Mangelinckx UGent and Norbert De Kimpe UGent (2011) JOURNAL OF ORGANIC CHEMISTRY. 76(1). p.234-244
abstract
alpha-Alkylation of N-sulfinyl imidates with 1-chloro-3-iodopropane successfully led to 2-substituted N-tert-butanesulfinyl-5-chloropentanimidates in acceptable diastereomeric ratios (dr 67/33 to 72/28) and good yields (74-86%). Subsequent reduction with NaBH4 led to the corresponding 2-substituted N-tert-butanesulfinyl-5-chloropentylamines, which could be cyclized to a range of new chiral 3-substituted N-tert-butanesulfinylpiperidines using NaH in DMSO. Finally, the N-tert-butanesulfinylpiperidines could be efficiently deprotected to enantiomerically pure 3-alkyl- and 3-arylpiperidine hydrochlorides.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
ENANTIOSELECTIVE SYNTHESIS, ABSOLUTE-CONFIGURATION, DOPAMINE-RECEPTOR, BICYCLIC LACTAMS, SUBSTITUTED (S)-PHENYLPIPERIDINES, ENANTIOPURE 3-ALKYLPIPERIDINES, DELTA-OXOESTERS, RECENT PROGRESS, NON-RACEMIC LACTAMS, DYNAMIC KINETIC RESOLUTION
journal title
JOURNAL OF ORGANIC CHEMISTRY
J. Org. Chem.
volume
76
issue
1
pages
234 - 244
Web of Science type
Article
Web of Science id
000285704000027
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
4.45 (2011)
JCR rank
9/56 (2011)
JCR quartile
1 (2011)
ISSN
0022-3263
DOI
10.1021/jo1020807
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
1116051
handle
http://hdl.handle.net/1854/LU-1116051
date created
2011-02-02 16:35:52
date last changed
2011-03-28 10:45:57
@article{1116051,
  abstract     = {alpha-Alkylation of N-sulfinyl imidates with 1-chloro-3-iodopropane successfully led to 2-substituted N-tert-butanesulfinyl-5-chloropentanimidates in acceptable diastereomeric ratios (dr 67/33 to 72/28) and good yields (74-86\%). Subsequent reduction with NaBH4 led to the corresponding 2-substituted N-tert-butanesulfinyl-5-chloropentylamines, which could be cyclized to a range of new chiral 3-substituted N-tert-butanesulfinylpiperidines using NaH in DMSO. Finally, the N-tert-butanesulfinylpiperidines could be efficiently deprotected to enantiomerically pure 3-alkyl- and 3-arylpiperidine hydrochlorides.},
  author       = {Colpaert, Filip and Mangelinckx, Sven and De Kimpe, Norbert},
  issn         = {0022-3263},
  journal      = {JOURNAL OF ORGANIC CHEMISTRY},
  keyword      = {ENANTIOSELECTIVE SYNTHESIS,ABSOLUTE-CONFIGURATION,DOPAMINE-RECEPTOR,BICYCLIC LACTAMS,SUBSTITUTED (S)-PHENYLPIPERIDINES,ENANTIOPURE 3-ALKYLPIPERIDINES,DELTA-OXOESTERS,RECENT PROGRESS,NON-RACEMIC LACTAMS,DYNAMIC KINETIC RESOLUTION},
  language     = {eng},
  number       = {1},
  pages        = {234--244},
  title        = {Asymmetric synthesis of chiral N-sulfinyl 3-alkyl- and 3-arylpiperidines by alpha-Alkylation of N-sulfinyl imidates with 1-Chloro-3-iodopropane},
  url          = {http://dx.doi.org/10.1021/jo1020807},
  volume       = {76},
  year         = {2011},
}

Chicago
Colpaert, Filip, Sven Mangelinckx, and Norbert De Kimpe. 2011. “Asymmetric Synthesis of Chiral N-sulfinyl 3-alkyl- and 3-arylpiperidines by alpha-Alkylation of N-sulfinyl Imidates with 1-Chloro-3-iodopropane.” Journal of Organic Chemistry 76 (1): 234–244.
APA
Colpaert, F., Mangelinckx, S., & De Kimpe, N. (2011). Asymmetric synthesis of chiral N-sulfinyl 3-alkyl- and 3-arylpiperidines by alpha-Alkylation of N-sulfinyl imidates with 1-Chloro-3-iodopropane. JOURNAL OF ORGANIC CHEMISTRY, 76(1), 234–244.
Vancouver
1.
Colpaert F, Mangelinckx S, De Kimpe N. Asymmetric synthesis of chiral N-sulfinyl 3-alkyl- and 3-arylpiperidines by alpha-Alkylation of N-sulfinyl imidates with 1-Chloro-3-iodopropane. JOURNAL OF ORGANIC CHEMISTRY. 2011;76(1):234–44.
MLA
Colpaert, Filip, Sven Mangelinckx, and Norbert De Kimpe. “Asymmetric Synthesis of Chiral N-sulfinyl 3-alkyl- and 3-arylpiperidines by alpha-Alkylation of N-sulfinyl Imidates with 1-Chloro-3-iodopropane.” JOURNAL OF ORGANIC CHEMISTRY 76.1 (2011): 234–244. Print.