Enantioselective Addition of Diethylzinc to Aldehydes Using Novel Chiral 1,4-aminoalcohols as Chiral Catalysts

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概要

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• A series of optically active 1,4-aminoalcohols were synthesized from the corresponding lactones, which were prepared from (+)-camphor and (-)-fenchone, via hydroxy amides. The addition reactions of diethylzinc to aldehydes using the 1,4-aminoalcohols as chiral catalysts were investigated. 1,4-Aminoalcohol catalysts derived from (+)-camphor resulted in secondary (S)-alcohols as the major product.    The 1,4-aminoalcohols bearing two propyl groups achieved the highest enantioselectivity; the enantiomeric excess was 95%. 1,4-Aminoalcohol catalysts derived from (-)-fencone resulted in secondary (R)-alcohols as the major product. In the chiral 1,4-aminoalcohols from (-)-fencone, the alcohol containing a morpholine structure appended to the amino group possessed the highest enantioselectivity; with an enantiomeric excess of 79%.

• 日本油化学会の論文

著者

• Mino Takashi

  Department Of Urban And Environmental Engineering University Of Tokyo

• FUJITA Tsutomu

  Department of Materials Technology, Faculty of Engineering, Chiba University

• Sakamoto Masami

  Graduate School Of Engineering Chiba Univ.

• Kasashima Yoshio

  Department Of Applied Chemistry Faculty Of Engineering Chiba University

• HANYU Naoto

  Graduate School of Science and Technology, Chiba University

• AOKI Tasuku

  Graduate School of Science and Technology, Chiba University

• Mino Takashi

  Department of Applied Chemistry and Biotechnology, Faculty of Engineering, Chiba University

• KASASHIMA Yoshio

  Department of Mechanical Science and Engineering, Faculty of Engineering, Chiba Institute of Technology

• Sakamoto Masami

  Graduate School of Science and Technology, Chiba University

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