219119-79-6Relevant academic research and scientific papers
Structure-enantioselectivity effects in 3,4-dihydropyrimido[2,1-b] benzothiazole-based isothioureas as enantioselective acylation catalysts
Belmessieri, Dorine,Joannesse, Caroline,Woods, Philip A.,MacGregor, Callum,Jones, Caroline,Campbell, Craig D.,Johnston, Craig P.,Duguet, Nicolas,Concellon, Carmen,Bragg, Ryan A.,Smith, Andrew D.
, p. 559 - 570 (2011)
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 ～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.
