1998 Fiscal Year Final Research Report Summary
Development of The Highly Effective System of Intramolecular Diels-Alder Reaction
| Project/Area Number |
09650963
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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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 | OKAYAMA UNIVERSITY |
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Principal Investigator |
ISHIKAWA Teruhiko Okayama University, Faculty of Engineering, Instructor, 工学部, 助手 (10263617)
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| Co-Investigator(Kenkyū-buntansha) |
SAITO Seiki Okayama University, Faculty of Engineering, Professor, 工学部, 教授 (60033239)
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| Project Period (FY) |
1997 – 1998
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| Keywords | hydroxamate / Diels-Alder reaction / stereoselectivity / transsition state |
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| Research Abstract |
In our efforts to explore intramolecular Diels-Alder systems which fulfill the four criteria, (1) easy connection between diene and dienophile parts (2) high reactivity, (3) homogeneous stereochemical consequences, and (4) high conventionality of the tethering group transformation, we have found that the above criteria can be established by utilizing hydroxamate-tethered systems.
In this system the diene and dienophile parts are close proximity, which is caused from lone-pair repulsion between two oxygen atoms and steric constraint around the N-O bond. Thus, the Intra-DA should be much more entropically favored.
These irreplaceable characteristics together with the extremely selective and predictable stereochemical consequences and the versatile latent functionality of the tethering group itself, make "temporary hydroxamate connection" attractive and promising. Application of this strategy to complex natural product synthesis is currently in progress.
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