2013 Fiscal Year Final Research Report

Development of the continuous functionalization reaction of the multiple bond utilizing organocatalysts

Research Project

Project/Area Number	24850005
Research Category	Grant-in-Aid for Research Activity Start-up
Allocation Type	Single-year Grants
Research Field	Organic chemistry
Research Institution	The University of Tokyo
Principal Investigator	HIRANO keiichi 東京大学, 薬学研究科(研究院), 助教 (40633392)
Project Period (FY)	2012-08-31 – 2014-03-31
Keywords	多置換オレフィン / アルキン / ジボリル化
Research Abstract	Development of highly efficient and regio-/stereoselective synthesis of tetrasubstituted olefins is one of important problems to be addressed in synthetic organic chemistry. We have developed the first highly trans-selective diborylation reaction of alkyne by designing a pseudo-intramolecular reaction between diboron and propargylic alcohol. By combining this diborylation methodology with Suzuki-Miyaura cross-coupling reaction, we demonstrated a straightforward and regio-controlled synthesis of a tetrasubsituted olefin in one pot. Moreover, diborylated products derived from propargylic alcohols possess the 1,2-oxaborol-2(5H)-ol structure, which has been attracting much attention as a potent pharmacophore against mycosis and others. We believe that this methodology will contribute to providing diverse new oxaborolol compounds and discovering a new type of boron-containing therapeutics.