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Stereoselective synthesis of chiral 4-(1-chloroalkyl)-β-lactams starting from amino acids and their transformation into functionalized chiral azetidines and pyrrolidines

Stijn Dekeukeleire UGent, Matthias D'hooghe UGent, Karl Törnroos and Norbert De Kimpe UGent (2010) JOURNAL OF ORGANIC CHEMISTRY. 75(17). p.5934-5940
abstract
Chiral short-chain alpha-chloroaldehydes were prepared starting from enantiomerically pure amino acids in a three-step approach, thus providing a practical synthetic alternative for known organo-catalytic alpha-chlorination procedures. The latter aldehydes proved to be useful starting materials for the stereoselective Staudinger synthesis of (3S,4S)-4-[(1S)-1-chloroalkyl]azetidin-2-ones in high diastereomeric ratios and good overall yields, which were used as chiral building blocks for the preparation of a number of azetidines and pyrrolidines.
Please use this url to cite or link to this publication:
author
organization
alternative title
Stereoselective synthesis of chiral 4-(1-chloroalkyl)-beta-lactams starting from amino acids and their transformation into functionalized chiral azetidines and pyrrolidines
year
type
journalArticle (original)
publication status
published
subject
keyword
RING EXPANSION, ASYMMETRIC ALPHA-CHLORINATION, STAUDINGER REACTION, ALDEHYDES, PIPERIDINE, FLUORINATION, ALKALOIDS, IMINES, ROUTE, BETA-LACTAMS
journal title
JOURNAL OF ORGANIC CHEMISTRY
J. Org. Chem.
volume
75
issue
17
pages
5934 - 5940
Web of Science type
Article
Web of Science id
000281180100018
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/jo101220q
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
1091527
handle
http://hdl.handle.net/1854/LU-1091527
date created
2010-12-22 16:20:37
date last changed
2016-12-19 15:45:03
@article{1091527,
  abstract     = {Chiral short-chain alpha-chloroaldehydes were prepared starting from enantiomerically pure amino acids in a three-step approach, thus providing a practical synthetic alternative for known organo-catalytic alpha-chlorination procedures. The latter aldehydes proved to be useful starting materials for the stereoselective Staudinger synthesis of (3S,4S)-4-[(1S)-1-chloroalkyl]azetidin-2-ones in high diastereomeric ratios and good overall yields, which were used as chiral building blocks for the preparation of a number of azetidines and pyrrolidines.},
  author       = {Dekeukeleire, Stijn and D'hooghe, Matthias and T{\"o}rnroos, Karl and De Kimpe, Norbert},
  issn         = {0022-3263},
  journal      = {JOURNAL OF ORGANIC CHEMISTRY},
  keyword      = {RING EXPANSION,ASYMMETRIC ALPHA-CHLORINATION,STAUDINGER REACTION,ALDEHYDES,PIPERIDINE,FLUORINATION,ALKALOIDS,IMINES,ROUTE,BETA-LACTAMS},
  language     = {eng},
  number       = {17},
  pages        = {5934--5940},
  title        = {Stereoselective synthesis of chiral 4-(1-chloroalkyl)-\ensuremath{\beta}-lactams starting from amino acids and their transformation into functionalized chiral azetidines and pyrrolidines},
  url          = {http://dx.doi.org/10.1021/jo101220q},
  volume       = {75},
  year         = {2010},
}

Chicago
Dekeukeleire, Stijn, Matthias D’hooghe, Karl Törnroos, and Norbert De Kimpe. 2010. “Stereoselective Synthesis of Chiral 4-(1-chloroalkyl)-β-lactams Starting from Amino Acids and Their Transformation into Functionalized Chiral Azetidines and Pyrrolidines.” Journal of Organic Chemistry 75 (17): 5934–5940.
APA
Dekeukeleire, S., D’hooghe, M., Törnroos, K., & De Kimpe, N. (2010). Stereoselective synthesis of chiral 4-(1-chloroalkyl)-β-lactams starting from amino acids and their transformation into functionalized chiral azetidines and pyrrolidines. JOURNAL OF ORGANIC CHEMISTRY, 75(17), 5934–5940.
Vancouver
1.
Dekeukeleire S, D’hooghe M, Törnroos K, De Kimpe N. Stereoselective synthesis of chiral 4-(1-chloroalkyl)-β-lactams starting from amino acids and their transformation into functionalized chiral azetidines and pyrrolidines. JOURNAL OF ORGANIC CHEMISTRY. 2010;75(17):5934–40.
MLA
Dekeukeleire, Stijn, Matthias D’hooghe, Karl Törnroos, et al. “Stereoselective Synthesis of Chiral 4-(1-chloroalkyl)-β-lactams Starting from Amino Acids and Their Transformation into Functionalized Chiral Azetidines and Pyrrolidines.” JOURNAL OF ORGANIC CHEMISTRY 75.17 (2010): 5934–5940. Print.