Asymmetric epoxidation, Michael addition, and triple cascade reaction using polymer-supported prolinol-based auxiliaries

Michael C. Varela, Seth M. Dixon, Kit Lam, Neil E. Schore

Research output: Contribution to journalArticle

54 Citations (Scopus)

Abstract

The applicability of polymer-supported diphenylprolinol derivatives in directing either asymmetric epoxidation or Michael addition of suitable α,β-unsaturated substrates has been assessed. Epoxidation of cinnamaldehyde in the solid state give poorer yields and stereoselectivities than in the solution-phase systems. In contrast Michael additions of several aldehyde enolates to 2-nitro-1-arylalkenes gave results that approached or surpassed those in solution, and could be extended successfully to a three-component Michael/Michael/aldol cascade process. Comparisons of the results of pendant- versus crosslinked functionalized resins in these applications were revealing of the benefits and limitations of each, as were attempts to reuse the polymer-bound auxiliaries.

Original languageEnglish (US)
Pages (from-to)10087-10090
Number of pages4
JournalTetrahedron
Volume64
Issue number43
DOIs
StatePublished - Oct 20 2008

Fingerprint

Epoxidation
Polymers
Stereoselectivity
Aldehydes
Resins
Derivatives
Substrates
prolinol
cinnamic aldehyde
diphenylprolinol
3-hydroxybutanal

Keywords

  • Crosslinking monomer
  • Diphenylprolinol
  • Enantioselective epoxidation
  • Enantioselective Michael addition
  • Polymer beads
  • Triple cascade reaction

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Asymmetric epoxidation, Michael addition, and triple cascade reaction using polymer-supported prolinol-based auxiliaries. / Varela, Michael C.; Dixon, Seth M.; Lam, Kit; Schore, Neil E.

In: Tetrahedron, Vol. 64, No. 43, 20.10.2008, p. 10087-10090.

Research output: Contribution to journalArticle

Varela, Michael C. ; Dixon, Seth M. ; Lam, Kit ; Schore, Neil E. / Asymmetric epoxidation, Michael addition, and triple cascade reaction using polymer-supported prolinol-based auxiliaries. In: Tetrahedron. 2008 ; Vol. 64, No. 43. pp. 10087-10090.
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