Chiral tetracyanocyclopentadienides for catalytic asymmetric reactions

2015 Fiscal Year Final Research Report

• Project/Area Number: 26860018
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Chemical pharmacy
• Research Institution: Meijo University
• Principal Investigator: Sakai Takeo 名城大学, 薬学部, 助教 (90583873)
• Project Period (FY): 2014-04-01 – 2016-03-31
• Keywords: 有機化学 / 超強酸共役塩基 / テトラシアノシクロペンタジエニド / 酸触媒 / 回転異性体

Outline of Final Research Achievements

Tetracyanocyclopentadienides having chiral binaphthyl auxiliaries has been developed as a new class of asymmetric superacid conjugate bases. The sodium tetracyanocyclopentadienides had a catalytic activity for a Mukaiyama aldol reaction and an addition reaction on acyl isoquinolinium salts, in which the reaction products had a few enantiomeric excess. In the chiral anions having an ester linker, two rotamers around C(Ar)-O bond in an aryl ester were observed at room temperature, that is a rare phenomenon for aryl esters. The rotation barriers were measured with a line-shape analysis on VT-NMR.

Free Research Field

有機合成化学