Control of planar, axial and helical chiralities based on the asymmetric ring-closing metathesis

2015 Fiscal Year Final Research Report

• Project/Area Number: 24550121
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Osaka Prefecture University
• Principal Investigator: Kamikawa Ken 大阪府立大学, 理学(系)研究科(研究院), 教授 (40316021)
• Project Period (FY): 2012-04-01 – 2016-03-31
• Keywords: asymmetric synthesis

Outline of Final Research Achievements

The molybdenum-catalyzed asymmetric ring-closing metathesis (ARCM) of the various Cs-symmetric (π-arene)chromium substrates proceeded smoothly and the corresponding bridged planar-chiral (π-arene)chromium complexes were obtained in excellent yields with excellent enantioselectivity of up to >99% ee. With a proper substituent, such as N-indolyl or 1-naphthyl, at the 2-positions of the η6-1,3-diisopropenylbenzene ligands, both biarylic axial chirality and π-arene-based planar-chirality could be simultaneously induced in the ARCM products via the double desymmetrization. The axial chirality thus induced was retained even after the removal of the chromium-carbonyl fragment, and the metal-free axially chiral biaryl/heterobiaryl compounds were obtained in up to >99% ee with complete retention of the enantiomeric purity. The overall protocol presented in this report can be regarded as a novel method of catalytically preparing axially chiral heterobiaryls/biaryl

Free Research Field

有機金属化学