Efficient Asymmetric Synthesis of Quasi-Natural Bioactive Compounds Having Contiguous All-Carbon Quaternary Stereocenters

2016 Fiscal Year Final Research Report

• Project/Area Number: 26410116
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Nagoya University
• Principal Investigator: Ohmatsu Kohsuke 名古屋大学, 工学研究科(WPI), 特任准教授 (00508997)
• Project Period (FY): 2014-04-01 – 2017-03-31
• Keywords: 不斉合成 / 反応開発 / 多連続不斉炭素 / キラル配位子 / パラジウム

Outline of Final Research Achievements

A Pd-catalyzed highly enantio- and diastereoselective [3+2] cycloaddition of 5-vinyloxazolidinones and activated trisubstituted alkenes has been successfully developed. This protocol for the single-step construction of densely functionalized pyrrolidines with three contiguous stereocenters including vicinal quaternary stereocenters depends on the remarkable ability of phosphine ligands possessing a chiral ammonium ion to promote intermolecular cycloaddition reactions with a precise control of absolute stereochemistry. A series of control experiments indicated that a chiral ammonium-phosphine hybrid ligand enabled the individual, yet simultaneous stereocontrol of each chiral center in the annulation reaction.

Free Research Field

有機合成化学