2012 Fiscal Year Final Research Report
Construction of Polycycles via Hydrogen Shift MediatedC(s p 3)-H bond functionalization.
| Project/Area Number |
22750044
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
Organic chemistry
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| Research Institution | Gakushuin University |
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Principal Investigator |
MORI Keiji 学習院大学, 理学部化学科, 助教 (10515076)
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| Project Period (FY) |
2010 – 2012
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| Keywords | 水素転位 / C-H結合官能基化 / 多環骨格 |
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| Research Abstract |
Whereasa range of related reactions of heteroatom-containing substrates (X = NR^2 or O) have been reported, the corresponding carbon analogue (X=CH2) had been overlooked until quite recently. We have disclosed that the benzylic C-H bond without an adjacent heteroatom could also participate in this type of transformation by selection of barbiturate as a electrophilic moiety, and the corresponding 3-aryltetraline derivatives were obtained in excellent chemical yield. Furthermore, we found thatt h I s reaction could be applied to an aliphatic substrates (without electronic assistance of adjacent heteroatom and arene).The asymmetric version of this type of reaction was also achieved by use of chiral phosphoric acid catalyst derived from BINOL. The synthetically useful tetrahydroquinoline derivatives were obtained with excellent enanioselectivities (over 90% ees).
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