Enantioselective Catalytic Domino Aza-Michael-Henry Reactions: One-Pot Asymmetric Synthesis of 3-Nitro-1,2-dihydroquinolines via Iminium Activation

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• 作者：Hao Luo ; Xilong Yan ; Ligong Chen ; Yang Li ; Na Liu and Guohui Yin
• 关键词：Organocatalysis ; Asymmetric catalysis ; Domino reactions ; Nitrogen heterocycles
• 刊名：European Journal of Organic Chemistry
• 出版年：2016
• 出版时间：March 2016
• 年：2016
• 卷：2016
• 期：9
• 页码：1702-1707
• 全文大小：905K
• ISSN：1099-0690

文摘

Asymmetric transformations arising from iminium activation of aromatic aldehydes are uncommon. In this work, an enantioselective organocatalytic domino aza-Michael–Henry reaction between N-(2-formylphenyl)sulfonamides and trans-β-nitro olefins through iminium activation has been presented. This reaction proceeded smoothly to give chiral 3-nitro-1,2-dihydroquinolines in high yields with up to 88 % ee under mild conditions. Furthermore, a preliminary study showed that 2-mercaptobenzaldehyde derivatives could participate in a thia-Michael–Henry reaction with trans-β-nitro olefins to yield chiral 3-nitro-2H-thiochromenes.