1995 Fiscal Year Final Research Report Summary
A Stereocontrolled Nucleophilic Addition to Imines and a Catalytic Asymmetric Reaction
| Project/Area Number |
06651010
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
Synthetic chemistry
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| Research Institution | Tokushima University |
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Principal Investigator |
WADA Makoto University of Tokushima Faculty of Integrated Arts and Sciences, Professor, 総合科学部, 教授 (10016173)
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| Project Period (FY) |
1994 – 1995
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| Keywords | beta-Amino alcohol / alpha-Siloxy aldimine / Imine / Allylation / Diastereoselectivity / Cyanation / alpha-Amino nitrile / Bismuth compound |
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| Research Abstract |
A stereocontrolled nucleophilic addition to imines and a catalytic asymmetric reaction are described as follows.
1. When alpha-siloxy aldimines were allowed to react with RLi followed by hydrolysis of the siloxy compounds, threo beta-amino alcohols were obtained stereoselectively. However, to our great suprise, the reaction of alpha-siloxy aldimines with RCu・BF_3 afforded erythro compounds exclusively.
2. Allylic bromides reacted with imines at 60ﾟC in acetonitrile to give the corresponding homoallylamines in good yields in the presence of bismuth trichloride-metallic zine. Diastereoselectivity of the present reaction was investigated by using crotyl bromide-imines or optically active imines-allyl bromide.
3. It was found that imines reacted with trimethylsilyl cyanide in the presence of a catalytic amount of bismuth trichloride to afford alpha-amino nitriles in good yields. Enantionselective cyanation of imines took place by using asymmetric bismuth compound prepared from optically active ethyl tartrate.
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