Stereoselective formation and rearrangement of morpholinium ylides derived from copper carbenoids |
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| Institution: | 1. Institute of Microelectronics & Department of Electrical Engineering, Center for Micro/Nano Science and Technology, Advanced Optoelectronic Technology Center, National Cheng Kung University, Tainan 70101, Taiwan;2. Department of Electrical Engineering, National University of Tainan, 700 Taiwan, Taiwan;1. Department of Chemistry, Ferdowsi University of Mashhad, Mashhad, Iran;2. Faculty of Chemistry, Kharazmi University, No. 49, Mofateh Ave., Tehran, Iran;3. Department of Chemistry, Faculty of Sciences, Shahid Beheshti University, G.C., PO Box 19396-4716, Evin, Tehran, Iran;1. Department of Chemistry, University of Delhi, North Campus, Delhi 110007, India;2. Chemistry Department, Faculty of Science, Umm Al-Qura University, 21955 Makkah, Saudi Arabia;3. Department of Chemistry, MNIT, Jaipur, Rajasthan 302017, India |
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| Abstract: | Amino diazoacetoacetates 4a–e and 7a,b were prepared from readily available amino alcohols and subjected to copper-catalyzed carbene-transfer reaction. Substrates 4c–e furnished the morpholin-2-ones 5c–e in good yield via the corresponding cyclic ammonium ylides, albeit with poor diastereoselectivity. Substrates 4a,b failed to provide the corresponding morpholinones, perhaps as a result of steric congestion. Cyclic substrates 7a,b underwent conversion to bicyclic morpholinones 8 and 9 in good yield and with moderate to good diastereoselectivity. This result is rationalized via control of the transiently stereogenic ammonium center of the intermediate bicyclic ylides. |
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