The Reaction of Electron-Deficient Cyclopropane Derivatives with Aromatic Amines |
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| Authors: | Yali Chen Weiguo Cao Meifei Yuan Huihui Wang Weiyu Ding Min Shao |
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| Institution: | 1. Department of Chemistry , Shanghai University , Shanghai, China Chenyali3@yahoo.com.cn;3. Department of Chemistry , Shanghai University , Shanghai, China;4. State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences , Shanghai, China;5. Department of Chemistry , Shanghai University , Shanghai, China |
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| Abstract: | Abstract N-Aryl-trans,trans-α-carboxyl-β-benzoyl-γ-aryl-γ-butyrolactams were synthesized in high yields with high stereoselectivity by the reaction of electron-deficient cyclopropane derivatives, cis-1-benzoyl-2-aryl-6,6-dimethyl-5,7-dioxo-spiro-2 (a)
Zhang , J. ;
Blazecka , P. G. ;
Davidson , J. G. First direct reductive amination of mucochloric acid: A simple and efficient method for preparing highly functionalized α,β-unsaturated γ-butyrolactams . Org. Lett. 2003 , 5 , 553 – 556 ; (b) Sarma, K. D.; Zhang, J.; Curran, T. T. Novel synthons from mucochloric acid: The first use of α,β-dichloro-γ-butenolides and γ-butyrolactams for direct vinylogous aldol addition. J. Org. Chem. 2007, 72, 3311–3318 . Google Scholar] 5 (a)
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Ding , W. Y. A simple approach to highly stereoselective synthesis of β γ-trans-γ-butyrolactones . Chem. J. Chin. Univ. 1998 , 19 , 1614 – 1616 ; (b) Chen, Y. L.; Ding, W. Y.; Cao, W. G.; Lu, C. Stereoselective synthesis of N-aryl-trans,trans-α-carboxyl-β-methoxycarbonyl-γ-aryl-γ-butyrolactones. Synth. Commun. 2002, 32, 1953–1960. Google Scholar]]-4,8-octadiones, with aromatic amines. The reaction mechanism was proposed. |
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| Keywords: | γ-Butyrolactam" target="_blank">γ-Butyrolactam cyclopropane derivative nucleophile reaction stereoselectivity |
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