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Stereoselectivity of the Honda-Reformatsky reaction in reactions with ethyl bromodifluoroacetate with alpha-oxygenated sulfinylimines

Clement Q. Fontenelle, Matthew Conroy, Mark Light, Thomas Poisson, Xavier Pannecoucke and Bruno Linclau (UGent)
(2014) JOURNAL OF ORGANIC CHEMISTRY. 79(9). p.4186-4195
Author
Organization
Abstract
The Reformatsky reaction of ethyl bromodifluoroacetate to alpha-oxygenated sulfinylimines is described. Using Honda-Reformatsky conditions, the reaction proceeds with double diastereodifferentiation, with the configuration of the sulfinyl group determining the stereochemical course of the reaction. Excellent diastereoselectivities (>94:6) are obtained for the matched cases. In contrast, reaction with sulfinylimines derived from unsubstituted alkanals proceeded with virtually no diastereoselectivity.
Keywords
BETA-AMINO-ACIDS, ASYMMETRIC-SYNTHESIS, ALPHA, ALPHA-DIFLUORO-BETA-AMINO, ACID, DIASTEREOSELECTIVE SYNTHESIS, DERIVATIVES, ALDEHYDES, ALCOHOLS, SULFINIMINES, FLUORINE, REAGENTS

Citation

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MLA
Fontenelle, Clement Q., et al. “Stereoselectivity of the Honda-Reformatsky Reaction in Reactions with Ethyl Bromodifluoroacetate with Alpha-Oxygenated Sulfinylimines.” JOURNAL OF ORGANIC CHEMISTRY, vol. 79, no. 9, 2014, pp. 4186–95, doi:10.1021/jo500396p.
APA
Fontenelle, C. Q., Conroy, M., Light, M., Poisson, T., Pannecoucke, X., & Linclau, B. (2014). Stereoselectivity of the Honda-Reformatsky reaction in reactions with ethyl bromodifluoroacetate with alpha-oxygenated sulfinylimines. JOURNAL OF ORGANIC CHEMISTRY, 79(9), 4186–4195. https://doi.org/10.1021/jo500396p
Chicago author-date
Fontenelle, Clement Q., Matthew Conroy, Mark Light, Thomas Poisson, Xavier Pannecoucke, and Bruno Linclau. 2014. “Stereoselectivity of the Honda-Reformatsky Reaction in Reactions with Ethyl Bromodifluoroacetate with Alpha-Oxygenated Sulfinylimines.” JOURNAL OF ORGANIC CHEMISTRY 79 (9): 4186–95. https://doi.org/10.1021/jo500396p.
Chicago author-date (all authors)
Fontenelle, Clement Q., Matthew Conroy, Mark Light, Thomas Poisson, Xavier Pannecoucke, and Bruno Linclau. 2014. “Stereoselectivity of the Honda-Reformatsky Reaction in Reactions with Ethyl Bromodifluoroacetate with Alpha-Oxygenated Sulfinylimines.” JOURNAL OF ORGANIC CHEMISTRY 79 (9): 4186–4195. doi:10.1021/jo500396p.
Vancouver
1.
Fontenelle CQ, Conroy M, Light M, Poisson T, Pannecoucke X, Linclau B. Stereoselectivity of the Honda-Reformatsky reaction in reactions with ethyl bromodifluoroacetate with alpha-oxygenated sulfinylimines. JOURNAL OF ORGANIC CHEMISTRY. 2014;79(9):4186–95.
IEEE
[1]
C. Q. Fontenelle, M. Conroy, M. Light, T. Poisson, X. Pannecoucke, and B. Linclau, “Stereoselectivity of the Honda-Reformatsky reaction in reactions with ethyl bromodifluoroacetate with alpha-oxygenated sulfinylimines,” JOURNAL OF ORGANIC CHEMISTRY, vol. 79, no. 9, pp. 4186–4195, 2014.
@article{01GMMX9BVTYV3110AVT03WNN3N,
  abstract     = {{The Reformatsky reaction of ethyl bromodifluoroacetate to alpha-oxygenated sulfinylimines is described. Using Honda-Reformatsky conditions, the reaction proceeds with double diastereodifferentiation, with the configuration of the sulfinyl group determining the stereochemical course of the reaction. Excellent diastereoselectivities (>94:6) are obtained for the matched cases. In contrast, reaction with sulfinylimines derived from unsubstituted alkanals proceeded with virtually no diastereoselectivity.}},
  author       = {{Fontenelle, Clement Q. and  Conroy, Matthew and  Light, Mark and  Poisson, Thomas and  Pannecoucke, Xavier and Linclau, Bruno}},
  issn         = {{0022-3263}},
  journal      = {{JOURNAL OF ORGANIC CHEMISTRY}},
  keywords     = {{BETA-AMINO-ACIDS,ASYMMETRIC-SYNTHESIS,ALPHA,ALPHA-DIFLUORO-BETA-AMINO,ACID,DIASTEREOSELECTIVE SYNTHESIS,DERIVATIVES,ALDEHYDES,ALCOHOLS,SULFINIMINES,FLUORINE,REAGENTS}},
  language     = {{eng}},
  number       = {{9}},
  pages        = {{4186--4195}},
  title        = {{Stereoselectivity of the Honda-Reformatsky reaction in reactions with ethyl bromodifluoroacetate with alpha-oxygenated sulfinylimines}},
  url          = {{http://doi.org/10.1021/jo500396p}},
  volume       = {{79}},
  year         = {{2014}},
}
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