Enantioselective and Regioselective Organocatalytic Conjugate Addition of Malonates to Nitroenynes |
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Authors: | Xiao‐Jiao Li Fang‐Zhi Peng Xiang Li Wen‐Tao Wu Zhong‐Wen Sun Ying‐Mei Li Shao‐Xiong Zhang Prof Dr Zhi‐Hui Shao |
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Institution: | Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091 (China), Fax: (+86)?871‐5035538 |
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Abstract: | The first catalytic asymmetric conjugate addition of 1,3‐dicarbonyl compounds to nitroenynes catalyzed by cinchona alkaloid‐based thiourea organocatalysts has been developed. The 1,4‐addition adducts were obtained solely, in moderate to good yields (up to 93 %) with good enantioselectivities (up to 99 % ee). This protocol affords a conceptually different entry to the precursors of pharmaceutically important chiral β‐alkynyl acid derivatives and synthetically useful chiral nitroalkynes. Notably, the protocol worked well with both aryl‐ and alkyl‐substituted alkynyl substrates. |
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Keywords: | asymmetric catalysis conjugate addition dicarbonyls enantioselectivity nitroenynes |
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