Synthesis and application of easily recyclable thiomorpholines for use in sulfur ylide mediated asymmetric epoxidation of aldehydes

Markus Hansch, Ona Illa Soler, Eoghan M. McGarrigle, Varinder K. Aggarwal*

*Corresponding author for this work

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

24 Citations (Scopus)

Abstract

Chiral nonracemic thiomorpholines have been synthesized in four to six steps from limonene or achiral alkenes using alpha-methylbenzylamine to control absolute stereochemistry. These aminosulfides have been used to generate sulfur ylides, which have been applied in the asymmetric epoxidation of aldehydes as easily recoverable catalysts. Excellent yields (up to 98%), enantioselectivities (up to 97:3 e.r.), and diastercoselectivities (>= 98:2 trans/cis) were achieved in these epoxidations and the sulfides were easily recovered in high yield (up to 97%) by simple acid/base extraction.

Translated title of the contributionSynthesis and Application of Easily Recyclable Thiomorpholines for use in Sulfur Ylide-mediated Asymmetric Epoxidation of Aldehydes
Original languageEnglish
Pages (from-to)1657-1663
Number of pages7
JournalChemistry - An Asian Journal
Volume3
Issue number8-9
DOIs
Publication statusPublished - Jul 2008

Bibliographical note

Publisher: WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • asymmetric epoxidation
  • enantioselectivity
  • sulfur
  • thiomorpholines
  • ylides
  • CARBONYL-COMPOUNDS
  • EPOXIDES
  • SULFIDES
  • DERIVATIVES
  • REAGENTS
  • SCOPE

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