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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

(2010) JOURNAL OF ORGANIC CHEMISTRY. 75(17). p.5934-5940
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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.
Keywords
RING EXPANSION, ASYMMETRIC ALPHA-CHLORINATION, STAUDINGER REACTION, ALDEHYDES, PIPERIDINE, FLUORINATION, ALKALOIDS, IMINES, ROUTE, BETA-LACTAMS

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Citation

Please use this url to cite or link to this publication:

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.
@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},
}

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