Dirhodium catalyzed intramolecular enantioselective C–H insertion reaction of N-cumyl-N-(2-p-anisylethyl)diazoacetamide: synthesis of (?)-Rolipram |
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| Institution: | 1. Institute for Advanced Study, Nanchang University, Nanchang, Jiangxi 330031, China;2. School of Chemistry, Nanchang University, Nanchang, Jiangxi 330031, China;1. Department of Pharmaceutical Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran;2. Department of Chemistry, Sharif University of Technology, Tehran, Iran |
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| Abstract: | Cumyl(2,2-dimethyl-benzyl) was used as an N-protecting group for intramolecular C–H insertion reaction of α-diazoacetamide. Excellent chemoselectivity (>98:2) in C–H insertion over the aromatic addition of N-cumyl-N-(2-p-anisylethyl)diazoacetamide was obtained with Rh2(4S)-MEOX)]4 catalyst in moderate enantioselectivity (53% ee). The reaction was successfully applied in the synthesis of (?)-Rolipram in 15% total yield. |
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