A Dynamic Kinetic Asymmetric Transformation in the α-Hydroxylation of Racemic Malonates and Its Application to Biologically Active Molecules

Authors

  • Dhande Sudhakar Reddy,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442
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  • Norio Shibata Prof.,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442
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  • Jun Nagai,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442
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  • Shuichi Nakamura Dr.,

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442
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  • Takeshi Toru Prof.

    1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5442
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  • Support was provided by KAKENHI (19390029), by a Grant-in-Aid for Scientific Research on Priority Areas “Advanced Molecular Transformations of Carbon Resources” from the Ministry of Education, Culture, Sports, Science, and Technology Japan (19020024).

Abstract

original image

Die chiralen α-Hydroxymalonate 2 sind durch α-Hydroxylierung der racemischen Malonate 1 mit dem Oxaziridin 3 mit hohen Ausbeuten und bis 98 % ee zugänglich, wenn der Nickel(II)-Komplex von (R,R)-DBFOX-Ph als Katalysator eingesetzt wird (siehe Schema). Dieses effiziente Verfahren wurde zur Synthese von Wirkstoffen genutzt.

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