Practical and Highly Selective Sulfur Ylide Mediated Asymmetric Epoxidations and Aziridinations Using an Inexpensive, Readily Available Chiral Sulfide. Applications to the Synthesis of Quinine and Quinidine

Ona Illa Soler, Muhammad Arshad, Abel Ros Lao, Eoghan M. McGarrigle, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

115 Citations (Scopus)

Abstract

Heating one of the most abundant naturally occurring inorganic chemicals (elemental sulfur) with one of the most readily available homochiral molecules (limonene) gives a one-step synthesis of a chiral sulfide which exhibits outstanding selectivities in sulfur ylide mediated asymmetric epoxidations and aziridinations. In particular reactions of benzyl and allylic sulfonium salts with both aromatic and aliphatic aldehydes gave epoxides with perfect enantioselectivities and the highest diastereoselectivities reported to date. In addition reactions with imines gave aziridines again with the highest enantioselectivities and diastereoselectivities reported to date. The reactions are scaleable, and the sulfide can be reisolated in high yield. The epoxidation has been used as the key step in a convergent and stereoselective synthesis of each of the diastereoisomers of the cinchona alkaloids, quinine and quinidine.

Translated title of the contributionPractical and Highly Selective Sulfur Ylide-Mediated Asymmetric Epoxidations and Aziridinations Using an Inexpensive and Readily Available Chiral Sulfide. Application to the Total Synthesis of Quinine and Quinidine
Original languageEnglish
Pages (from-to)1828 - 1830
Number of pages5
JournalJournal of the American Chemical Society
Volume132
Issue number6
DOIs
Publication statusPublished - 17 Feb 2010

Keywords

  • COREY-CHAYKOVSKY REACTION
  • IN-SITU GENERATION
  • ENANTIOSELECTIVE SYNTHESIS
  • STEREOSELECTIVE-SYNTHESIS
  • CARBONYL-COMPOUNDS
  • N-SULFONYLIMINES
  • PHOSPHAZENE BASE
  • EPOXIDES
  • ALDEHYDES
  • ALKALOIDS

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