Structure-enantioselectivity effects in 3,4-dihydropyrimido[2,1-b]-benzothiazole-based isothioureas as enantioselective acylation catalysts

Dorine Belmessieri, Caroline Joannesse, Philip A. Woods, Callum MacGregor, Caroline Jones, Craig D. Campbell, Craig P. Johnston, Nicolas Duguet, Carmen Concellon, Ryan A. Bragg, Andrew D. Smith

Research output: Contribution to journalArticlepeer-review

66 Citations (Scopus)

Abstract

The catalytic activity and enantioselectivity in the kinetic resolution of (+/-)-1-naphthylethanol with a range of structurally related 3,4-dihydropyrimido[2,1-b]benzothiazole-based catalysts is examined. Of the isothiourea catalysts screened, (2S,3R)-2-phenyl-3-isopropyl substitution proved optimal, giving good levels of selectivity in the kinetic resolution of a number of secondary alcohols (S values up to > 100 at similar to 50% conversion). Low catalyst loadings (0.10-0.25 mol%) of the optimal isothiourea can be used to generate enantiopure alcohols (>99% ee) in good yields.

Original languageEnglish
Pages (from-to)559-570
Number of pages12
JournalOrganic & Biomolecular Chemistry
Volume9
Issue number2
DOIs
Publication statusPublished - 2011

Keywords

  • NONENZYMATIC KINETIC RESOLUTION
  • N-HETEROCYCLIC CARBENES
  • ACYL TRANSFER CATALYSTS
  • CHIRAL PHOSPHINE CATALYSTS
  • C-CARBOXYL TRANSFER
  • ASYMMETRIC ACYLATION
  • SECONDARY ALCOHOLS
  • SEC-ALCOHOLS
  • NUCLEOPHILIC CATALYSIS
  • PROPARGYLIC ALCOHOLS

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