1993 Fiscal Year Final Research Report Summary
Development of Highly Stereoselective Reaction in Metal and Hetero-Atom Combined Reaction Filed
| Project/Area Number |
04453098
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| Research Category |
Grant-in-Aid for General Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
Synthetic chemistry
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| Research Institution | KYOTO UNIVERSITY |
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Principal Investigator |
UTIMOTO Kiitiro Kyoto University, Material Chemistry, Professor, 工学部, 教授 (90025958)
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| Co-Investigator(Kenkyū-buntansha) |
MATSUBARA Seijiro Kyoto University, Material Chemistry, Instructor, 工学部, 助手 (90190496)
OSHIMA Koichiro Kyoto University, Material Chemistry, Professor, 工学部, 教授 (00111922)
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| Project Period (FY) |
1992 – 1993
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| Keywords | Lanthonoids Reagent / Diastereoselectivity / Optically Active Amine / 1,4-Addition / beta-Keto Amide / Organomanganese Reagent / β-ケトアミド / 有機マンガン反応剤 |
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| Research Abstract |
(1) An addition of various organolithium compounds to imine or hydrazine derived from optically active 2-formy1-1,3-oxathiane gave amine derivatives with high diastereoselectivity (>99% de) in good yields.
(2) Diastereoselective 1,4-addition reaction of optically active 2-butenoy1-1,3-oxathiane was studied. The addition of organocupper reagent in the presence of YbCl_3 provided 1,4-adduct as a single diastercomeric compound. On the other hand, treatment with organomagnesium reagent in the presence of a catalytic amount of CuBr gave the other diastereomer with high diastereoselectivity.
(3) Lanthanoid triflate proved to be a good catalyst for the 1,4-addition reaction of various amines to alpha, beta-unsaturated esters. The reaction was succesfully applied to a diastereoselective synthesis of optically active beta-lactams.
(4) Stereoselective alkylation of 2-alky1-2-formylamide with alky1-aluminium dichloride was achieved. An addition of trialkylaluminium or alkylmanganese chloride to 2-methy1-3-oxo-amide gave the corresponding 3-hydroxy-2-methylamide with high stereoselectivity.
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