2002 Fiscal Year Final Research Report Summary
Development of a New Stereospecific Allylation and Its Application for Synthesis
| Project/Area Number |
12450357
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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 |
有機工業化学
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| Research Institution | Okayama University of Science |
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Principal Investigator |
NOKAMI Junzo Okayama Univ. of Sci., Applied Chem., Prof., 工学部, 教授 (70109742)
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| Project Period (FY) |
2000 – 2002
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| Keywords | allyl-transfer reaction / homoallylic alcohol / alk-2-enylation / chiral auxiliary / asymmetric synthesis / menthone / [3.3]-sigmatropy / six-membered chair-like transition state |
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| Research Abstract |
To date, there have been no reported methods for effectively synthesizing homoallylic alcohols via alk-2-enylation of an aldehyde. On the other hand, we recently discovered the first convenient and highly stereoselective but-2-enylation of an aldehyde via an ally-transfer reaction due to [3.3]-sigmatropy rearrangement. Further, we demonstrated the possibility of alk-2-enylation of an aldehyde via an allyl-transfer reaction using optically active menthone as a chiral auxiliary. We also discovered that this improved the yield of the product due to an increase in the length of the alkyl chains.
Prop-2-enylation of an aldehyd via an allyl-transfer reaction is a valuable reaction is a valuable reaction, particularly for asymmetric syntheses. This discovery makes it possible to efficiently synthesize optically pure poly-substituted tetrahydropyrane derivatives using an optically active homoallylic alcohol. In turn, it also becomes possible to efficiently synthesize many bioactive compounds and their analogues in optically active forms.
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