Development of highly selective asymmetric photoreactions controlled by the structure of ionic liquids

2015 Fiscal Year Final Research Report

• Project/Area Number: 25870437
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Organic chemistry; Synthetic chemistry
• Research Institution: Nara Institute of Science and Technology
• Principal Investigator: NISHIYAMA Yasuhiro 奈良先端科学技術大学院大学, 物質創成科学研究科, 助教 (00581430)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Keywords: イオン液体 / 不斉光反応 / キラルテンプレート / キラリティ制御 / メンチル基 / イミダゾリウムカチオン / アンモニウムカチオン / アニオン交換

Outline of Final Research Achievements

In this research, we aimed for the highly enantioselective photoreaction by using chiral ionic liquids, which structure can be controlled as desired, as chiral template. Because menthol derivatives as chiral auxiliaries successfully proceed the highly diastereoselective photoreactions, we synthesized the chiral ionic liquid possessing both the menthyl group and imidazolium group; however, no chiral induction was observed. In case of the ammonium salt having the menthyl group, chiral ionic liquids could not be synthesized. On the other hand, the primary ammonium salt having the menthyl group can cause the enantioselective photoreaction. Furthermore, the chirality of the obtained major product is different from the chirality of the major product obtained by the primary menthyl amine. This result means the functional group of chiral template can control the product chirality although the product chirality is usually controlled by the chirality of chiral template.

Free Research Field

有機光化学