Organocatalyzed Intramolecular Michael Addition Reaction
碩士 === 國立臺灣師範大學 === 化學系 === 102 === Asymmetric organocatalytic Michael addition has attracted interests due to its environmental friendliness and the generation of multiple stereogenic centers in a single step. In this study‚ treatment of (E)-5-nitro-6-arylhex-5-en-2-one using a catalytic amount of...
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| Format: | Others |
| Language: | zh-TW |
| Published: |
2014
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| Online Access: | http://ndltd.ncl.edu.tw/handle/37268852645833421689 |
| Summary: | 碩士 === 國立臺灣師範大學 === 化學系 === 102 === Asymmetric organocatalytic Michael addition has attracted interests due to its environmental friendliness and the generation of multiple stereogenic centers in a single step. In this study‚ treatment of (E)-5-nitro-6-arylhex-5-en-2-one using a catalytic amount of quinine-derived primary amine (20 mol%) and 4-dimethyl aminopyridine (20 mol%) in 1,4-dioxane and DMSO (1:1) at 50 oC to give 3,4-trans-
disubstituted cyclohexanones via intramolecular Michael addition process with moderate chemical yields and high-to-excellent stereoselectivities (>95:5 dr and up to 96% ee). We describe a rapid and practical synthetic route involving six-step reaction toward the synthesis of (-)-Epibatidine
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