Innovation in Synthesis of Heterocycles Utilizing 1,3-Dipoles

2015 Fiscal Year Final Research Report

• Project/Area Number: 24350022
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Partial Multi-year Fund
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Kanazawa University
• Principal Investigator: Yutaka Ukaji 金沢大学, 物質化学系, 教授 (80193853)
• Co-Investigator(Renkei-kenkyūsha): SOETA TAKAHIRO 金沢大学, 物質化学系, 准教授 (10506819)
• Project Period (FY): 2012-04-01 – 2016-03-31
• Keywords: 1,3-双極子 / 複素環 / 協奏的付加環化 / 段階的付加－環化 / 共役拡張型1,3-双極子 / 1,5-双極子 / 光学活性

Outline of Final Research Achievements

The development of a practical and efficient method for construction of heterocycles is an essential part of programs to explore new medical and agrochemical agents. 1,3-Dipoles are important chemical species containing heteroatoms. We studied on innovative syntheses heterocycles utilizing 1,3-dipoles based on three strategies.
We designed a novel chiral reaction system possessing multi-metal centers utilizing tartaric acid ester as a chiral auxiliary. Based on this concept, we developed asymmetric 1,3-dipolar cycloadditions of azomethine imines to allylic alcohols. A strategy consisted of a stepwise addition to 1,3-dipoles, followed by cyclizaion was found to be an alternative and regiocontrolled pathway to synthesize of heterocycles. An asymmetric addition of acetylides to nitrones followed by cyclization was developed to give the corresponding optically active 4-isoxazolines. A novel [5+1] cycloaddition reaction of N’-acyl azomethine imines with isocyanides was also explored.

Free Research Field

有機合成化学