Structure-enantioselectivity effects in 3,4-dihydropyrimido[2,1-b]benzothiazole-based isothioureas as enantioselective acylation catalysts |
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Authors: | Belmessieri Dorine Joannesse Caroline Woods Philip A MacGregor Callum Jones Caroline Campbell Craig D Johnston Craig P Duguet Nicolas Concellón Carmen Bragg Ryan A Smith Andrew D |
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Institution: | EastCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, UK. |
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Abstract: | The catalytic activity and enantioselectivity in the kinetic resolution of (±)-1-naphthylethanol with a range of structurally related 3,4-dihydropyrimido2,1-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. |
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