Catalytic Asymmetric Synthesis of Phosphine Derivatives with a Stereogenic Phosphorus Atom

2015 Fiscal Year Final Research Report

• Project/Area Number: 26620074
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry
• Research Institution: Hokkaido University
• Principal Investigator: OGASAWARA Masamichi 北海道大学, 触媒科学研究所, 准教授 (70301231)
• Project Period (FY): 2014-04-01 – 2016-03-31
• Keywords: 触媒的不斉合成 / リン / 中心不斉 / メタセシス / 非対称化 / モリブデン / クロム

Outline of Final Research Achievements

We have achieved the formal asymmetric cross-metathesis between an alkenylbenzene derivative and a bis(methallyl)phosphine by the use of a chiral molybdenum-alkylidene catalyst giving the phosphine drivative with a stereogenic phosphorus atom in up to 95% ee. Our strategy is the use of a chromium fragment as a template, in which the two reactants are preinstalled onto the chromium metal. The chromium complexes thus obtained were employed as substrates for the asymmetric ring-closing metathesis and the subsequent de-chromation reaction afforded the acyclic metal-free phosphine derivatives with the perfect chemo-selectivity and the Z-selectivity.

Free Research Field

有機金属化学