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Synthesis of stereodefined piperidines from aziridines and their transformation into conformationally constrained amino acids, amino alcohols and 2,7-diazabicyclo[3.3.1]nonanes

Karel Vervisch UGent, Matthias D'hooghe UGent, Karl Törnroos and Norbert De Kimpe UGent (2010) JOURNAL OF ORGANIC CHEMISTRY. 75(22). p.7734-7744
abstract
2-(2-Cyano-2-phenylethyl)azindines were converted into novel cis- and trans-2-chloromethyl-4-phenylpiperidine-4-carbonitriles via alkylation with 1-bromo-2-chloroethane followed by microwave-assisted 6-exo-tet cyclization and regiospecific ring opening The latter piperidines were used as eligible substrates for the synthesis of stereodefined 2-chloromethyl-, 2-hydroxymethyl-, and 2-carboxymethyl-4-phenylpiperidine-4-carboxylic acids, 2-hydroxymethyl-4-phenylpiperidine-4-carbonitriles, 3-hydroxy-5-phenylazepane-5-carbonitriles, and 5-phenyl-2,7-diazabicyclo[3 3 1]nonanes
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
ASYMMETRIC-SYNTHESIS, RING-OPENING REACTIONS, EFFICIENT METHOD, DERIVATIVES, CHEMISTRY, SALTS, AFFINITY, RECEPTOR, ANALOGS, 1-ALKYL-2-(BROMOMETHYL)AZIRIDINES
journal title
JOURNAL OF ORGANIC CHEMISTRY
J. Org. Chem.
volume
75
issue
22
pages
7734 - 7744
Web of Science type
Article
Web of Science id
000284080300026
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
4.002 (2010)
JCR rank
8/56 (2010)
JCR quartile
1 (2010)
ISSN
0022-3263
DOI
10.1021/jo101646u
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
1091563
handle
http://hdl.handle.net/1854/LU-1091563
date created
2010-12-22 16:51:39
date last changed
2011-12-01 00:30:28
@article{1091563,
  abstract     = {2-(2-Cyano-2-phenylethyl)azindines were converted into novel cis- and trans-2-chloromethyl-4-phenylpiperidine-4-carbonitriles via alkylation with 1-bromo-2-chloroethane followed by microwave-assisted 6-exo-tet cyclization and regiospecific ring opening The latter piperidines were used as eligible substrates for the synthesis of stereodefined 2-chloromethyl-, 2-hydroxymethyl-, and 2-carboxymethyl-4-phenylpiperidine-4-carboxylic acids, 2-hydroxymethyl-4-phenylpiperidine-4-carbonitriles, 3-hydroxy-5-phenylazepane-5-carbonitriles, and 5-phenyl-2,7-diazabicyclo[3 3 1]nonanes},
  author       = {Vervisch, Karel and D'hooghe, Matthias and T{\"o}rnroos, Karl and De Kimpe, Norbert},
  issn         = {0022-3263},
  journal      = {JOURNAL OF ORGANIC CHEMISTRY},
  keyword      = {ASYMMETRIC-SYNTHESIS,RING-OPENING REACTIONS,EFFICIENT METHOD,DERIVATIVES,CHEMISTRY,SALTS,AFFINITY,RECEPTOR,ANALOGS,1-ALKYL-2-(BROMOMETHYL)AZIRIDINES},
  language     = {eng},
  number       = {22},
  pages        = {7734--7744},
  title        = {Synthesis of stereodefined piperidines from aziridines and their transformation into conformationally constrained amino acids, amino alcohols and 2,7-diazabicyclo[3.3.1]nonanes},
  url          = {http://dx.doi.org/10.1021/jo101646u},
  volume       = {75},
  year         = {2010},
}

Chicago
Vervisch, Karel, Matthias D’hooghe, Karl Törnroos, and Norbert De Kimpe. 2010. “Synthesis of Stereodefined Piperidines from Aziridines and Their Transformation into Conformationally Constrained Amino Acids, Amino Alcohols and 2,7-diazabicyclo[3.3.1]nonanes.” Journal of Organic Chemistry 75 (22): 7734–7744.
APA
Vervisch, K., D’hooghe, M., Törnroos, K., & De Kimpe, N. (2010). Synthesis of stereodefined piperidines from aziridines and their transformation into conformationally constrained amino acids, amino alcohols and 2,7-diazabicyclo[3.3.1]nonanes. JOURNAL OF ORGANIC CHEMISTRY, 75(22), 7734–7744.
Vancouver
1.
Vervisch K, D’hooghe M, Törnroos K, De Kimpe N. Synthesis of stereodefined piperidines from aziridines and their transformation into conformationally constrained amino acids, amino alcohols and 2,7-diazabicyclo[3.3.1]nonanes. JOURNAL OF ORGANIC CHEMISTRY. 2010;75(22):7734–44.
MLA
Vervisch, Karel, Matthias D’hooghe, Karl Törnroos, et al. “Synthesis of Stereodefined Piperidines from Aziridines and Their Transformation into Conformationally Constrained Amino Acids, Amino Alcohols and 2,7-diazabicyclo[3.3.1]nonanes.” JOURNAL OF ORGANIC CHEMISTRY 75.22 (2010): 7734–7744. Print.