1999 Fiscal Year Final Research Report Summary
Allylindation of Cyclopropenes Stereochemically Regulated by the Chelation
| Project/Area Number |
10640518
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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 |
Organic chemistry
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| Research Institution | Nagoya Institute of Technology |
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Principal Investigator |
ARAKI Shuki Nagoya Institute of Technology, Faculty of Engineering, Professor, 工学部, 教授 (30115670)
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| Co-Investigator(Kenkyū-buntansha) |
KAWAI Masao Nagoya Institute of Technology, Faculty of Engineering, Professor, 工学部, 教授 (60161270)
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| Project Period (FY) |
1998 – 1999
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| Keywords | Indium / Allylation / Cyclopropene / Cyclopropane / Chelation / Norbornenol / Stereoselectivity / Regioselectivity |
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| Research Abstract |
The chelation effects of a hydroxy group on the reactivities and selectivities have systematically been studied in the addition reactions of allylindium reagents (allylindation) to cyclopropenes and related compounds possessing a hydroxy group.
The cyclopropenes bearing a hydroxy group in the 3-position chelate readily to allylindium reagents giving allylindation products highly regio- and stereoselectively. In the allylindation of the cyclopropenes with a hydroxyalkyl group at the 1-position, the selectivities depend largely on the length of the hydroxyalkyl chain. Thus, the selectivities are found to be switched by the location of the hydroxy group. Further, changing the allylindium reagents and the reaction solvents nicely regulated the selectivities. The structure of the allylindation product, cyclopropylindium, has fully been characterized by X-ray crystallography.
Norbornenol derivatives possessing a strained carbon-carbon double bond also underwent clean allylindation, where the hydroxy group accelerates the allylindation as well as controls high regio- and stereoselectivities.
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