Enantioselective synthesis of (S)-timolol via kinetic resolution of terminal epoxides and dihydroxylation of allylamines

Srinivasarao V. Narina, Arumugam Sudalai

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22 Scopus citations

Abstract

An efficient enantioselective synthesis of (S)-timolol has been described using chiral Co-salen-catalyzed kinetic resolution of less expensive (±)-epichlorohydrin with 3-hydroxy-4-(N-morpholino)-1,2,5-thiadiazole in good overall yield (55%) and excellent enantioselectivity (98%). Synthesis of (S)-timolol has also been achieved using hydrolytic kinetic resolution as well as asymmetric dihydroxylation routes in 90% ee and 56% ee, respectively.

Original languageEnglish (US)
Pages (from-to)3026-3030
Number of pages5
JournalTetrahedron
Volume63
Issue number14
DOIs
StatePublished - Apr 2 2007

Bibliographical note

Funding Information:
S.V.N. thanks CSIR, New Delhi, for research fellowships. The authors would also like to thank Dr. B. D. Kulkarni, Head, CE-PD Division, for his constant encouragement and support.

Copyright:
Copyright 2019 Elsevier B.V., All rights reserved.

Keywords

  • Asymmetric reactions
  • Diols
  • Epoxides
  • Kinetic resolution
  • Oxazolidinone

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