D and/or 13C Labeled 1,3–Dithiane

By: Lisa Roth, ChemFiles Volume 11 Article 1

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

Unlabeled 1,3–Dithiane is a versatile reagent able to act as an acyl anion equivalent when submitted to Corey-Seebach reaction conditions.1 This well known chemistry can also be carried out when 1,3–Dithiane is labeled at the 2 position providing labeled and protected aldehydes, ketones, α-hydroxyketones, 1,2–diketones and α-keto acid derivatives. Deprotection can be facilitated using standard methods to give the appropriately labeled substrates (Scheme 1).2

Scheme 1: 1,3–Dithiane for the introduction of D and/or 13C.

New Labeled D and/or 13C 1,3–Dithiane

(716111), (716073)


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Materials

     

References

  1. a) Seebach, D.; Corey, E. J.; J. Org. Chem. 1975, 40, 231. (b) Mundy, P. B.; Ellerd, M. G.; Favaloro, F. G., Jr.; Name Reactions and Reagents in Organic Synthesis, 2nd ed.; Wiley & Sons: New York, 2005; p 186, 745.
  2. Wutz, P. G. M.; Greene, T. W.; Protection for the Carbonyl Group, Greene’s Protective Groups in Organic Synthesis, 4th ed.; Wiley & Sons: New York, 2007; p 482.

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