1,6-Remote Asymmetric Induction in ε-Substituted α, γ-dienones

• Project/Area Number: 11640553
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Kurashiki University of Science and the Arts
• Principal Investigator: SATO Tsuneo Kurashiki University of Science and the Arts, College of Science and Industrial Technology, Professor, 産業科学技術学部, 教授 (80183383)
• Project Period (FY): 1999 – 2000
• Project Status: Completed (Fiscal Year 2000)
• Budget Amount: ¥2,700,000 (Direct Cost: ¥2,700,000); Fiscal Year 2000: ¥1,100,000 (Direct Cost: ¥1,100,000); Fiscal Year 1999: ¥1,600,000 (Direct Cost: ¥1,600,000)
• Keywords: remore asymmetric induction / substituent effect / ε-substituted-α, γ-dienone / reduction / alkylation / ε-置換α、γ-ジエノン

Research Abstract

1. (4E,6E)-2,2,9,9-Tetramethyl-4,6-decadien-3-ones having five kinds of heteroatom-substituents at 8 position were synthesized in multiple steps and their 1,6-remote asymmetric reductions were examined with a series of reducing agents at -78 ℃.
2. The structures of ε-substituted α, γ-dienones described above in solution at room temperature were examined by means of IR (CCl_4) and ^1H NMR (CDCl_3).
3. No 1,6-remote asymmetric inductions were observed in the reactions of (2E,4E)-7,7-dimethyl-6-phenylthio-2,4-octadienal with t-butyl organometallic reagents.