Development of Chiral Magnesium and Aluminum Catalysts for Practically Fast Enantioselective Carbonyl Addition Reaction

2017 Fiscal Year Final Research Report

• Project/Area Number: 15K05500
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Kyoto Institute of Technology
• Principal Investigator: Harada Toshiro 京都工芸繊維大学, 分子化学系, 教授 (30135628)
• Co-Investigator(Kenkyū-buntansha): 楠川 隆博 京都工芸繊維大学, 分子化学系, 准教授 (70300720)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Keywords: 不斉触媒 / 不斉合成 / 不斉付加反応

Outline of Final Research Achievements

Chiral aluminum catalyst system has been developed for the enantioselective vinylation of aldehydes. Disubstituted (E)-vinylaluminum reagents, generated regio- and stereoselectively by the carboalumination of terminal alkynes with trimethylaluminum, were used straightforwardly without transmetalation to vinyltitanium reagents in subsequent enantioselective addition to aldehydes with a 3,5-diphenylphenyl-H8-BINOL-derived chiral aluminum catalyst at low catalyst loading (5 mol%). The reaction afforded the corresponding enantiomerically enriched secondary allylic alcohols with a reversal of selectivity observed in closely relevant reactions catalyzed by a chiral titanium complex derived from the same ligand.

Free Research Field

有機合成化学