2003 Fiscal Year Final Research Report Summary

GENERATION OF αTRIFLUOROMETHYLATED ENOLATE SPECIES AND THEIR APPLICATION TO ASYMMETRIC ALDOL SYNTHESIS

Research Project

Project/Area Number	14550808
Research Category	Grant-in-Aid for Scientific Research (C)
Allocation Type	Single-year Grants
Section	一般
Research Field	有機工業化学
Research Institution	Kyoto Institute of Technology
Principal Investigator	ISHIHARA Takashi KYOTO INSTITUTE OF TECHNOLOGY, DEPARTMENT OF CHEMISTRY AND MATERIALS TECHNOLOGY, PROFESSOR, 工芸学部, 教授 (40093182)
Project Period (FY)	2002 – 2003
Keywords	α-trifluoromethylated enolate species / fluorinated α-bromopropanoic acid derivatives / phosphine-lewis acid / asymmetric aldol-type reaction / reductive coupling reaction / erythro-selectivity / diastereoselectivity
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.

(4 results)