On the scope of diastereoselective epoxidation of various chiral auxiliaries derived enones: The conformational analysis of camphor derived N- and O-enones

Wei Der Lee, Ching Chen Chiu, Hua Lin Hsu, Kwunmin Chen

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Various camphor derived N- and O-enones were treated with selected oxidants to provide the corresponding epoxides in a wide range of diastereoselectivity. For camphorsultam derived activated alkenes, high to excellent stereoselectivities were obtained when the s-trans enones were treated with methyl(trifluoromethyl)dioxirane. On the other hand, for exo-10,10-diphenyl-2, 10-camphanediol (3) and exo-10,10-diphenyl-10-methoxy-2-camphanol (4) derived alkenes, the use of s-cis enones gave the desired epoxide with excellent diastereoselectivity under the same reaction conditions. The stereoselectivity was highly dependent on the geometry of the auxiliaries derived enones and the stereochemical induction is discussed.

Original languageEnglish
Pages (from-to)6657-6664
Number of pages8
JournalTetrahedron
Volume60
Issue number31
DOIs
Publication statusPublished - 2004 Jul 26

Fingerprint

Camphor
Stereoselectivity
Epoxidation
Epoxy Compounds
Alkenes
Oxidants
Geometry
diphenyl
camphorsultam
methyl(trifluoromethyl)dioxirane

Keywords

  • Asymmetric epoxidation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

On the scope of diastereoselective epoxidation of various chiral auxiliaries derived enones : The conformational analysis of camphor derived N- and O-enones. / Lee, Wei Der; Chiu, Ching Chen; Hsu, Hua Lin; Chen, Kwunmin.

In: Tetrahedron, Vol. 60, No. 31, 26.07.2004, p. 6657-6664.

Research output: Contribution to journalArticle

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