Development of hydrogen bond-donating asymmetric Lewis acid catalyst for control of multiple selectivities

2018 Fiscal Year Final Research Report

• Project/Area Number: 17H07164
• Research Category: Grant-in-Aid for Research Activity Start-up
• Allocation Type: Single-year Grants
• Research Field: Synthetic chemistry
• Research Institution: Rikkyo University
• Principal Investigator: TSUTSUMI Ryosuke 立教大学, 理学部, 助教 (90801697)
• Project Period (FY): 2017-08-25 – 2019-03-31
• Keywords: 有機合成化学 / 不斉合成 / ルイス酸

Outline of Final Research Achievements

In the course of investigating the simultaneous control of regio- and stereoselectivity using hydrogen bond-donating chiral Lewis acids, we found that the reaction between γ-butenolide and α-ketoester proceeded at the α-position of γ-butenolide in the presence of bifunctional organobase catalyst. We newly designed a chiral 2,2'-bipyridine-type ligand with a side chain bearing urea functional group as a hydrogen bond donor. This hydrogen bond-donating chiral Lewis acid was found to catalyze various stereoselective reactions.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

化合物が持つ本質的な性質に左右されない位置選択性、あるいは触媒制御による位置異性体の作り分けが実現できれば、既存の方法では実現できない新しい有機化合物の合成法の立案につなげられる可能性がある。今回、ルイス酸と水素結合との協同効果によりこれを達成するべく、新規不斉配位子を設計・開発した。本研究成果は、反応基質が持つ複数の反応点を識別可能な配位子設計へと発展させるための端緒となる。