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Paper | Regular issue | Vol 63, No. 6, 2004, pp.1345-1357
Published online, 16th April, 2004
DOI: 10.3987/COM-04-10056
A Study of Structure and Dynamics of Prochiral N-C Axis for Asymmetric Transition Metal Catalysis, with Phosphorous-31 (V) by 3D NMR Spectroscopy Combined with MO Calculation

Yohko Sakamoto,* Kazuhiro Kondo, Maiko Tokunaga, Kumiko Kazuta, Hiroko Fujita, Yasuoki Murakami, and Toyohiko Aoyama

*School of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan


We have synthesized five kinds of prochiral N-C axis for asymmetric transition metal catalysis with phosphorus-31 (V) and investigated their mobility in solution by measuring 31P NMR spin-lattice relaxation time (T1). 1-(S)-N-[2-(diphenylphosphinyl)naphthyl-2-(hydroxylmethyl)pyrrolidine; compound (1b), and 1-(S)-N-[2-(diphenylphosphinyl)naphthyl]-2-(pyrrolidinyl- methyl pyrroridine; compound (1e) was assigned on the basis of NMR spectral data. From the vicinal 31PÅ]1H and 1HÅ]13C coupling constants of J resolution spectra on the 3D NMR spectra, the dihedral angles of compounds (1b), and (1e) were determined. The optimum stable structures of these compounds were obtained on the basis of NMR spectral data combined with molecular orbital calculalations.