Asymmetric synthesis of 1-acyl-3,4-disubstituted pyrrolidine-2-boronic acid derivatives |
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| Affiliation: | 1. Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, 150040 Harbin, China;2. State Engineering Laboratory for Bioresource Eco-Utilization, Northeast Forestry University, 150040 Harbin, China;1. Natural Products Chemistry Division, CSIR-North East Institute of Science and Technology, Jorhat, Assam 785006, India;2. Academy of Scientific and Innovative Research (AcSIR), CSIR-North East Institute of Science and Technology, Jorhat, Assam 785006, India;3. Analytical Chemistry Division, CSIR-North East Institute of Science and Technology, Jorhat, Assam 785006, India;1. Division of Microbiology, Department of Pathology and Laboratory Medicine, Nova Scotia Health, Halifax, Nova Scotia, Canada;2. Department of Pathology, Dalhousie University, Halifax, Nova Scotia, Canada;3. Departments of Medicine, Dalhousie University, Halifax, Nova Scotia, Canada;4. Departments of Microbiology and Immunology, Dalhousie University, Halifax, Nova Scotia, Canada;5. Provincial Public Health Laboratory Network of Nova Scotia (PPHLN), Halifax, Nova Scotia, Canada |
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| Abstract: | An analogue of N-acetylkainic acid having a cyano group and a boronic acid group in place of the two carboxyl groups has been synthesized with high stereocontrol via a series of chain extensions of pinanediol [(trityloxy)methyl]boronate with (dihalomethyl)lithium followed by appropriate nucleophilic substitution of the resulting chloro or bromo boronic ester. Substituents were introduced in the order isopropenyl, cyanomethyl, and bis(trimethylsilyl)amino. The last of these was converted to acetamido, the hydroxyl function was unmasked and mesylated, and the pyrrolidine ring was closed. Attempts to carry out further chain extension on the boronic ester resulted in low yields, evidently the highly polar amido substituent interferes with the (dichloromethyl)lithium insertion process. |
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