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Takada H, Metzner P, Philouze C. First chiral selenium ylides used for asymmetric conversion of aldehydes into epoxides. Chem Commun (Camb). 2001;(22):2350-1doi: 10.1039/b106063p.
Takada, H., Metzner, P., & Philouze, C. (2001). First chiral selenium ylides used for asymmetric conversion of aldehydes into epoxides. Chemical communications (Cambridge, England), (22), 2350-1. https://doi.org/10.1039/b106063p
Takada, H, et al. "First chiral selenium ylides used for asymmetric conversion of aldehydes into epoxides." Chemical communications (Cambridge, England) vol. ,22 (2001): 2350-1. doi: https://doi.org/10.1039/b106063p
Takada H, Metzner P, Philouze C. First chiral selenium ylides used for asymmetric conversion of aldehydes into epoxides. Chem Commun (Camb). 2001 Nov 21;(22):2350-1. doi: 10.1039/b106063p. PMID: 12240070.
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Chem Commun (Camb). 2001 Nov 21;(22):2350-1. doi: 10.1039/b106063p.

First chiral selenium ylides used for asymmetric conversion of aldehydes into epoxides.

Chemical communications (Cambridge, England)

H Takada, P Metzner, C Philouze

Affiliations

  1. Laboratoire de Chimie Moléculaire et Thio-organique (UMR CNRS 6507), ISMRA-Université, 6, boulevard du Maréchal Juin, 14050 Caen, France.

PMID: 12240070 DOI: 10.1039/b106063p

Abstract

Enantioenriched selenonium ylides have been generated by addition of benzyl bromide to C2 symmetric (2R,5R)-2,5-dimethylselenolane in the presence of NaOH, and subsequently reacted with a variety of aldehydes to give oxiranes with excellent enantiomeric excesses (a catalytic version has been achieved); also, an aliphatic cyclic hypervalent dibromoselenurane structure has been demonstrated by X-ray analysis.

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