The combination of domino process and kinetic resolution: Organocatalytic synthesis of functionalised cyclopentenes by sequential S N2′- Michael reaction

Lun Fu Yeh, Shaik Anwar, Kwunmin Chen

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

An interesting combination of organocatalytic cascade reaction and kinetic resolution was developed for the synthesis of functionalised cyclopentenes by sequential S N2′-Michael process. Treatment of the racemic nitroallylic acetates with glutaraldehyde in the presence of diphenylprolinol silyl ether to give tetrasubstituted cyclopentenes with high to excellent stereoselectivities (up to 96% ee and 12:1 dr). The less reactive enantiomeric substrates were generally recovered with good to excellent optical purities (up to 99% ee).

Original languageEnglish
Pages (from-to)7317-7321
Number of pages5
JournalTetrahedron
Volume68
Issue number36
DOIs
Publication statusPublished - 2012 Sep 9

Fingerprint

Cyclopentanes
Stereoselectivity
Kinetics
Glutaral
Acetates
Substrates
diphenylprolinol silyl ether

Keywords

  • Cascade
  • Cyclopentene
  • Kinetic resolution
  • Michael reaction
  • Organocatalysis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

The combination of domino process and kinetic resolution : Organocatalytic synthesis of functionalised cyclopentenes by sequential S N2′- Michael reaction. / Yeh, Lun Fu; Anwar, Shaik; Chen, Kwunmin.

In: Tetrahedron, Vol. 68, No. 36, 09.09.2012, p. 7317-7321.

Research output: Contribution to journalArticle

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