Minoru Inagaki
Kyoto University
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Publication
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Journal of The Chemical Society-perkin Transactions 1 | 1987
Jun Hiratake; Minoru Inagaki; Yukio Yamamoto; Jun'ichi Oda
Asymmetric ring-opening of prochiral acid anhydrides (1) with methanol has been achieved by a catalytic quantity of cinchona alkaloids (2). The product, the optically active half-ester (3), has been subjected to functional-group-selective reduction to give the optically active lactones (5). The reaction rate of the ring-opening and the extent of selectivity are dependent on the nature of the reaction medium, the polarity of solvent, and substrate concentration. By selecting the reaction conditions, an enantiometric excess of up to 70% has been obtained. The kinetic isotope effect and other mechanistic investigations suggest that the reaction proceeds via general-base catalysis by the quinuclidine moiety of the base (2), and that the relative configuration of the C-9 hydroxy group with respect to the C-8 quinuclidine amino function determines the selectivity of the reaction.
Journal of Organic Chemistry | 1992
Minoru Inagaki; Jun Hiratake; Takaaki Nishioka; Jun'ichi Oda
Journal of Organic Chemistry | 1988
Jun Hiratake; Minoru Inagaki; Takaaki Nishioka; Jun'ichi Oda
Journal of the American Chemical Society | 1991
Minoru Inagaki; Jun Hiratake; Takaaki Nishioka; Jun'ichi Oda
Bulletin of the Chemical Society of Japan | 1987
Minoru Inagaki; Jun Hiratake; Yukio Yamamoto; Jun'ichi Oda
Agricultural and biological chemistry | 1989
Minoru Inagaki; Jun Hiratake; Takaaki Nishioka; Jun'ichi Oda
Bulletin of the Chemical Society of Japan | 1992
Minoru Inagaki; Akihiko Hatanaka; Mitsuo Mimura; Jun Hiratake; Takaaki Nishioka; Jun'ichi Oda
Journal of the American Chemical Society | 1997
Maki Uragami; Takehisa Dewa; Minoru Inagaki; Robert A. Hendel; Steven L. Regen
Journal of the American Chemical Society | 1997
Minoru Inagaki; Motonari Shibakami; Steven L. Regen
Journal of the American Chemical Society | 1998
Motonari Shibakami; Minoru Inagaki; Steven L. Regen
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National Institute of Advanced Industrial Science and Technology
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