Lewis acid-mediated SN2 type displacement by grignard reagents on chiral perhydropyrido[2,1-b]pyrrolo[1,2-d][1,3,4]oxadiazine. Chirality induction in asymmetric synthesis of 2-substituted piperidines
摘要：
Et2AlCl-mediated nucleophilic alkylation with Grignard reagents on chiral perhydropyrido[2,1-b]pyrrolo[1,2-d][1,3,4]oxadiazine has proved to proceed via an SN2 mechanism at low temperatures (below 80 °C) with high to excellent inversive stereoselection, while, at an elevated temperature, hydrazonium ions are formed preferentially leading to retentive stereoselection. This methodology provides useful access to enantioselective preparation of 2-substituted piperidines and is used for asymmetric synthesis of (+)-coniine.
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DOI：
10.1016/S0040-4039(97)00991-X
年份：
1997
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