1992 Fiscal Year Final Research Report Summary
The Production of Chiral beta-Aminoalcohols to be excellent catalysts for the synthesis of optically active sec-alcohols.
| Project/Area Number |
03559005
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| Research Category |
Grant-in-Aid for Developmental Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
広領域
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| Research Institution | YAMAGUCHI UNIVERSITY |
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Principal Investigator |
OGUNI Nobuki YAMAGUCHI UNIVERSITY,DEPARTMENT OF CHEMISTRY,PROFESSOR, 理学部, 教授 (60028165)
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| Co-Investigator(Kenkyū-buntansha) |
NAKAGAWA Tatsuji TOSOH-AKZOIND,RESEARCH MANAGER, 研究課長
IKEDA Yoshihiko TOSOH-AKZOIND,RESEARCHER, 研究員
HAYASHI Masahiko YAMAGUCHI UNIVERSITY,DEPARTMENT OF CHEMISTRY,ASSOCIATE PROFESSOR, 理学部, 助教授 (60192704)
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| Project Period (FY) |
1991 – 1992
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| Keywords | optically active beta-aminoalcohols / asymmetric reaction / optical resolution / asymmetric alkylation of aldehydes |
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| Research Abstract |
The synthetic methods of optically active sec-alcohols are knwon that asymmetric reductions of unsymmetrical ketones or the asymmetric alkylation of aldehydes are useful methods. The author found the asymmetric alkylation method of aldehydes with dialkylzinc catalyzed by beta-aminoalcohols in 1983. For the first time we studied the synthetic method of optically active 2-hydroxy-3,3-dimethyl-butylamine which was excellent catalysts for alkylation of aldehydes. High yield production ofmonobromination or monochlorination of pinacolone was succeeded by the reaction at 0ﾟC.The reduction of monohalogeno-pinacolone was performed by NaBH_4 in MeOH-H_2O,followed by treatment of alkalline to give t-butylethylene oxide. Thus, obtained t-butylethylene oxide was reacted with N-magnesium salt of sec-amines to give N-dialkyl-2-hydroxy-3,3-dimethyl-1-butylamines in high yield. By this method a variety of beta-aminoalcohols could be prepared.
Rac-beta-aminoalcohols was resolved by Sharpless asymmetric oxidation which was very useful method for resolving beta-aminoalcohols. The production of optically active beta-amino-alcohols in industrial scale is now in pending, because the demand of the products is now in step of researching.
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