Synthesis of optically active atropisomeric aminophosphine and its application to catalytic asymmetric reaction

ORGN 776

Takashi Mino, tmino@faculty.chiba-u.jp, Youichi Tanaka, Masami Sakamoto, and Tsutomu Fujita. Department of Applied Chemistry and Biotechnology, Chiba University, Faculty of Engineering, 1-33 Yayoi, Inage, Chiba, 263-8522, Japan
The aminophosphines 1 have been easily prepared from 1,2,3,4-tetrahydroquinoline or indoline and their atropisomeric enantiomers were observed by using HPLC-CD on a chiral phase. In some cases, the resolution of each enantiomers was successfully completed by column chromatography of the diastereomeric complexes formed with chiral palladium reagent. In the presence of chiral aminophosphine 1, palladium-catalyzed asymmetric allylic alkylation was carried out. This reaction proceeded successfully with good enantioselectivity.

 

Asymmetric Reactions, Molecular Recognition, Self Assembly, Bioorganic Chemistry, Process R&D
8:00 PM-10:00 PM, Wednesday, 16 March 2005 Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005