2005 Fiscal Year Final Research Report Summary
Development of asymmetric reactions using multi-reagent complexes
| Project/Area Number |
15390005
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Kyoto University |
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Principal Investigator |
TOMIOKA Kiyoshi Kyoto University, Professor, 薬学研究科, 教授 (50114575)
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| Co-Investigator(Kenkyū-buntansha) |
IIDA Akira Kyoto University, Associate Professor, 薬学研究科, 助教授 (40202816)
YAMADA Ken-ichi Kyoto University, Assistant Professor, 薬学研究科, 助手 (00335184)
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| Project Period (FY) |
2003 – 2005
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| Keywords | lithium enolate / chiral diether ligand / Taxol / asymmetric addition / aryllithium / tandem reactions / (-)-lycorine / chiral amidophosphine |
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| Research Abstract |
1)A precursor of Taxol side chain was stereoselectively synthesized in high yield by the oxidation of the dianion resulting from the asymmetric addition of a chiral lithium enolate, derived from a chiral acetate, to N-PMP imine in the presence of a lithum amide.
2)A formal total synthesis of (-)-1-deoxylycorine was achieved using tandem conjugate addition-cyclization reaction of aryllithium and alkenoate controled by a chiral ligand.
3)5-Arylcyclohexenones and trans-3,6-disubstituted cyclohexanons were synthesized with high stereoselectivity in good yields using an amidophosphane-rhodium catalyzed asymmetric addition of arylborane reagents to substituted cyclohexenones.
4)Chiral amino alcohol controlled asymmetric addition of alkynylzincs to nitroalkenes and aldehydes was developed.
5)Chiral oxazoline ligand controlled catalytic asymmetric intramolecular hydroamination was developed.
6)Chiral amidophosphane ligand controlled asymmetric addition of dialkylzincs to nitroalkene was developed.
7)A formal synthesis of (+)-halichlorine was achieved using tandem Michael addition-alkylation protocol controlled by a chiral diether ligand.
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[Book] ブルース有機化学2004
Author(s)
P.Y.Bruice
Total Pages
1529
Publisher
化学同人
Description
「研究成果報告書概要(和文)」より
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