2003 Fiscal Year Final Research Report Summary
GENERATION OF αTRIFLUOROMETHYLATED ENOLATE SPECIES AND THEIR APPLICATION TO ASYMMETRIC ALDOL SYNTHESIS
| Project/Area Number |
14550808
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
有機工業化学
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| Research Institution | Kyoto Institute of Technology |
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Principal Investigator |
ISHIHARA Takashi KYOTO INSTITUTE OF TECHNOLOGY, DEPARTMENT OF CHEMISTRY AND MATERIALS TECHNOLOGY, PROFESSOR, 工芸学部, 教授 (40093182)
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| Project Period (FY) |
2002 – 2003
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| Keywords | α-trifluoromethylated enolate species / fluorinated α-bromopropanoic acid derivatives / phosphine-lewis acid / asymmetric aldol-type reaction / reductive coupling reaction / erythro-selectivity / diastereoselectivity |
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| Research Abstract |
When N-methoxy-N-methyl-2-bromo-2, 3, 3, 3-tetrafluropropanamide was allowed to react with various aldehydes under the influence of triphenylphosphine and a catalytic amount of titanium (IV) isopropoxide in dichloromethane at room temperature, (trifluoromethyl)-β-hydroxy amides preferentially in good to excellent yields.
In addition, the reactions of benzyl 2-bromo-2, 3, 3, 3-tetrafluoropro-panoate with various types of chiral imines, such as (S)-sulfinimines and imines derived from (S)-valine methyl ester or (S)-phenylglycine methyl ester, in the presence of zinc in tetrahydrofuran at room temperature were revealed to afford the threo-and erythro-isomers of α-fluoro-α-(trifluoromethyl) -β-amino esters with high diasteremeric excesses in fair to good chemical yields.
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