Stereoselective Synthesis of Cyclic Alkaloids Using the Cation Pool Method

2015 Fiscal Year Final Research Report

• Project/Area Number: 25410117
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Okayama University
• Principal Investigator: SUGA SEIJI 岡山大学, 自然科学研究科, 教授 (50291430)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Keywords: 選択的合成 / イミニウムカチオン / アルカロイド / カチオンプール法 / 電解酸化

Outline of Final Research Achievements

The purpose of the present research is to reveal the mechanistic insight of diastereoselective synthesis of di-substituted piperidine derivatives accomplished by the reaction of N-acyliminium ions, which are prepared by the Indirect Cation Pool Method. The reactions of highly reactive N-acyliminium ions having a piperidine skeleton with a substituent, generated and accumulated from the corresponding thioaminals by the treatment of electrochemically generated arylsulfonium ion pool, with carbon nucleophiles gave rise to the formation of the corresponding of di-substituted piperidine derivatives in a highly-stereoselective manner. We validated the relationship of the conformations of cationic intermediates and stereoselectivities. The conformations of the N-acyliminium ions were determined by NMR spectroscopy, and the origin of the stereoselectivity was mostly clarified.

Free Research Field

化学