Stereoselective synthesis of spiro[5.5]undecane derivatives via biocatalytic [5+1] double Michael additions |
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| Affiliation: | 1. College of Food Science, Fujian Agriculture and Forestry University, Fuzhou, 350002, China;2. MOE Laboratory of Biosystems Homeostasis & Protection, College of Life Sciences, Zhejiang University, Hangzhou, Zhejiang, 310058, China;3. College of Food Science and Nutritional Engineering, China Agricultural University, Beijing, 100083, China;4. Department of Pharmacy, State University of Bangladesh, Dhaka, 1205, Bangladesh;5. Institute of Chinese Medical Sciences, State Key Laboratory of Quality Research in Chinese Medicine, University of Macau, Macau |
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| Abstract: | A novel enzymatic, promiscuous protocol of d-aminoacylase (DA)-catalyzed [5+1] double Michael addition was developed herein, for the synthesis of (hetero)spiro[5.5]undecane derivatives in moderate yields. It is notable that almost only the cis isomers were obtained through this biocatalytic methodology in all the cases according to their 1H and 13C NMR spectra. It is the first report on hydrolase-catalyzed double Michael addition in organic solvent. |
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| Keywords: | Double Michael addition Spiro compounds Enzyme Stereoselectivity |
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