Asymmetric Hydrogenation Catalyzed by Rhodium Complex with a New Chiral Bisphosphine Derived from L-Threonine

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概要

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• A new chiral bisphosphine, (2R, 3S)-1,2-bis (diphenylphosphino)-3-^tBoc-aminobutane (RS-5), was prepared from L-threonine. Mesylation of ^tBoc-L-threonine methyl ester (2) and subsequent reduction with sodium borohydride gave the alcohol (10), which was treated with potassium carbonate to afford a key intermediate, (2S, 3S)-1-^tBoc-3-methyl-2-aziridinemethanol (SS-7b). Mesylation of SS-7b, followed by treatment with sodium diphenylphosphide afforded the new chiral bisphosphine (RS-5). The structure of RS-5 was confirmed by the X-ray analysis of its crystalline CuCl complex (RS-12). The cationic rhodium (I) complexes prepared from RS-5 and RS-12 are efficient asymmetric hydrogenation catalysts for N-acyldehydroamino acids, giving (S)-N-acylamino acids in high optical yields (83-94% ee).

• 社団法人日本薬学会の論文
• 1985-04-25

著者

• 伊達 忠正

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,

• 西條 成良

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 斉藤 邦夫

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 小寺 啓司

  Organic Chemistry Research Laboratory and Analytical Center, Tanabe Seiyaku Co., Ltd.

• 斉藤 邦夫

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 小寺 啓司

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co Ltd.

• 西條 成良

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 伊達 忠正

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

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