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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

Sly like a “DBFOX”: The chiral α-hydroxy malonate 2 can be prepared in high yield and with up to 98 % ee from racemic malonate 1 through α-hydroxylation using oxaziridine 3 and is catalyzed by the (R,R)-DBFOX-Ph/NiII complex (see scheme). Biologically useful molecules have been prepared by using this method and illustrate its efficiency.

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