Enantioselective one-pot conjugate addition of grignard reagents to cyclic enones followed by amidomethylation |
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Authors: | Bilčík Filip Drusan Michal Marák Jozef Šebesta Radovan |
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Institution: | Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina CH-2, SK-84215 Bratislava, Slovakia. |
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Abstract: | Enantioselective conjugate addition of Grignard reagents to enones, catalyzed by Cu-Taniaphos or Josiphos complex, affords chiral enolates. Ensuing one-pot Mannich reaction with TiCl(4)-generated imine leads to aminocarbonyl compounds with benzyloxycarbonyl-protected nitrogen. Both diastereomers of these compounds are isolated in moderate yields but high enantiomeric purities (up to er 97.5:2.5). |
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