Polystyrene-supported N-sulfonylated amino alcohols and their applications to titanium(IV) complexes catalyzed enantioselective diethylzinc additions to aldehydes

Xin Ping Hui, Chien An Chen, Kuo Hui Wu, Han Mou Gau

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

Crosslinked polystyrene-supported resins 4, 7a, and 7b containing N-sulfonylated β-amino alcohol in 98, 20, and 40% loadings are prepared. Asymmetric diethylzinc additions to benzaldehyde employing titanium complexes of 10 mol % resins 4, 7a, or 7b are examined and the best performed 7a/Ti(O-i-Pr)4 catalytic system applies to various aldehydes to afford desired secondary alcohols in excellent enantioselectivities up to 95% ee. The resin 7a is reused five times, giving the product with enantioselectivities >86% ee and an 81% ee is obtained when the resin is used the sixth time. The used resin 7a is refreshed with 1 M HCl and the asymmetric reaction employing the regenerated resin 7a gives the product in 88% ee.

Original languageEnglish
Pages (from-to)10-15
Number of pages6
JournalChirality
Volume19
Issue number1
DOIs
StatePublished - 2007

Keywords

  • Aldehyde
  • Asymmetric ethylation
  • Diethylzinc
  • N-sulfonylated β-amino alcohol
  • Polystyrene-supported catalyst
  • Titanium(IV) complex

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