2012 Fiscal Year Final Research Report

Development of a Novel Synthetic Method for Chiral NitrogenContaining Compounds under Photoirradiation

Research Project

Project/Area Number	23750107
Research Category	Grant-in-Aid for Young Scientists (B)
Allocation Type	Multi-year Fund
Research Field	Synthetic chemistry
Research Institution	Shinshu University
Principal Investigator	ITOH Kennosuke 信州大学, 工学部, 助教 (40467874)
Project Period (FY)	2011 – 2012
Keywords	選択的合成 / 反応
Research Abstract	Direct functionalization of sp^3C-H bond adjuscent to nitrogen atom of tertiary amines under photoirradiation has been emerged a particularly attractive synthetic approach for nitrogen-containing compounds. We have recently developed the novel intermolecular addition of α-aminoalkyl radicals with nitrones under photoirradiation in the absence of photosensitizers to give hydroxylamine derivatives. The combined use of photosensitizers and photoirradiation works in a highly effective manner to accelerate reactions of α-aminoalkyl radical with nitrones. Several kinds of nitrones and tertiary amines have been successfully utilized under photosensitized conditions. A multifunctional chiral hybrid Lewis acid-photosensitizer catalyst has been developed and used for the reaction to give the adduct in a good yield. The enantiomeric excess of the product has not been unknown because of difficulties in determination of the optimal conditions for the separation of the enantiomers by chiral HPLC.