13C Labeled Olefination Reagents

By: Lisa Roth, ChemFiles Volume 11 Article 1

Lisa Roth, Ph.D.
Product Manager
lisa.roth@sial.com

The 13C labeled olefination reagents1 were developed to simplify the labeling process by providing a set of substrates ready to be incorporated into precedented chemical syntheses.2 These olefination reagents provide access to a fi xed 13C label within the alkene as well as site-variable deuterium incorporation (Scheme 1). This methodology efficiently provides a densely labeled compound ready for further functionalization.

Scheme 1: Olefination reagents labeling strategies.


The availability of all three sulfur oxidation states allows control of the reaction conditions including base type and strength as well as access to a preferred sulfur removal strategy.3 By providing access to mild reaction conditions, fewer compatibility issues arise between reaction conditions, olefination reagent and substrate.

New 13C Labeled Olefination Reagents:

(715832), (715824), (715816)

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Materials

     

References

  1. Licensed from Highlands Stable Isotopes Corp.
  2. a) Capela, R.; Oliveira, R.; Gonçalves, L. M.; Domingos, A; Gut, J.; Rosenthal, P. J.; Lopes, F.; Moreira, R.; Biorg. Med. Chem. Lett. 2009, 19, 3229. (b) Verissimo, E.; Berry, N.; Gibbons, P.; Cristiano, M. L. S.; Rosenthal, P. J.; Gut, J.; Ward, S. A.; O’Neill, P. M.; Biorg. Med. Chem. Lett. 2008, 18, 4210.
  3. a) Beye, G. E.; Ward, D. E.; J. Am. Chem. Soc. 2010, 132, 7210. (b) Pellissier, H.; Tetrahedron 2006, 62, 5559.

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