2004 Fiscal Year Final Research Report Summary
Development of Novel Carbanion Rearrangements as a Stereoselective Approach toward Heteroatom-containing Natural Products
| Project/Area Number |
14350473
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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 |
Synthetic chemistry
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| Research Institution | Tokyo Institute of Technology |
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Principal Investigator |
TOMOOKA Katsuhiko Tokyo Institute of Technology, Department of Applied Chemistry, Associate Professor, 大学院・理工学研究科, 助教授 (70207629)
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| Project Period (FY) |
2002 – 2004
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| Keywords | carbanion / asymmetric synthesis / rearrangement / acetal / cyclic ether / pyrrole |
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| Research Abstract |
The following novel carbanion reactions of hetero-functionalized system have been developed.
I.Oxy system
a)Ring-enlarging [2,3]-Wittig rearrangement of cyclic acetals : Stereoselective approach to medium-sized cyclic vinyl ethers.
b)Ring-contracting [1,2]-Wittig rearrangement of cyclic acetals : Stereoselective approach to medium-sized cyclic ethers.
c)Anionic ring-contraction reaction of cyclic acetal system : Stereoselective approach to multi-functionalized oxetanes.
d)[1,4]-Wittig rearrangement containing ethynylvinylmethanol-derived migration terminus : Tandem rearrangement-aldol reaction.
II.Aza system
a)Ring-enlarging aza-[1,2] and [2,3]-rearrangement of cyclic hemiaminals.
b)Asymmetric aza-Wirtig rearrangement induced by Sn-Li transmetalation.
c)The sequential carbanion reactions of phthalimide-derived alkynyl hemiaminal: Efficient approach to polysubstituted pyrrole via four components coupling.
d)Stevens rearrangement of a cyclic hemiacetal system: Diastereoselective approach to chiral α-amino ketone.
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Research Products
(13 results)
