Stereoselective Reduction of (S)-4-Isopropyl-3-phenacyl-1,3-oxazolidin-2-one by Means of 1,4-Asymmetric Induction : Synthesis of Chiral 2-Amino-1-phenylethanols

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概要

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• Stereoselective reductions of (S)-4-isopropyl-3-phenacyl-1,3-oxazolidin-2-one (2) with several complex metal hydrides gave 2-4'-isopropyl-2'-oxo-1', 3'-oxazolidinyl-1-phenylethanol (3) and 2-N-1'-isopropyl-2'-hydroxyethyl-N-methylamino-1-phenylethanol (4) in good yields. These products were diastereomeric mixtures and the diastereomer ratios were estimated to be ca. 75 : 25. The asymmetric 2-amino-1-phenylethanols (major products of 3 and 4) were easily isolated by recrystallization. The absolute configuration of (1S, 4'S)-3 was determined by X-ray analysis. The reductions of (S)-4-isopropyl-1-phenacyl-1,3-oxazolidine (6) with complex metal hydrides gave 2-4'-isopropyl-1', 3'-oxazolidinyl-1-phenylethanol (7) and 4 as diastereomeric mixtures (ca. 70 : 30).

• 社団法人日本薬学会の論文
• 1985-01-25

著者

• 高橋 浩

  Faculty Of Pharmaceutical Science Hoshi University

• 河合 賢一

  Faculty Of Pharmaceutical Sciences Hoshi University

• 河合 賢一

  Institute of Medicinal Chemistry, Hoshi University

• 高橋 浩

  Institute of Medicinal Chemistry, Hoshi University

• 山田 宜之

  Institute of Medicinal Chemistry, Hoshi University

• 東山 公男

  Institute of Medicinal Chemistry, Hoshi University

• 東山 公男

  星薬科大学医薬品化学研究室

• 山田 宜之

  Institute Of Medicinal Chemistry Hoshi University

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