2013 Fiscal Year Final Research Report
Development of the innovative organic synthesis based on the hydrogen autotransfer process
| Project/Area Number |
23550122
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Synthetic chemistry
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| Research Institution | Osaka University |
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Principal Investigator |
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| Co-Investigator(Kenkyū-buntansha) |
ZHOU Da-yang 大阪大学, 産業科学研究所, 助教 (00324848)
ASANO Kaori 大阪大学, 産業科学研究所, 助教 (00311762)
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| Co-Investigator(Renkei-kenkyūsha) |
SASAI Hiroaki 大阪大学, 産業科学研究所, 教授 (90205831)
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| Project Period (FY) |
2011 – 2013
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| Keywords | タンデム反応 / アルドール反応 / ジオール / アルデヒド / 不斉触媒 / イリジウム |
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| Research Abstract |
Asymmetric tandem coupling of meso-diols with aldehydes was achieved by using a chiral iridium catalyst. This tandem reaction consists of oxidative desymmetrization of the meso-diol, aldol condensation with an aldehyde, and reduction of the enone intermediate. A one-pot method using an excess of a hydrogen donor gave a-benzyl-b-hydroxyindan-1-ones in <94% ee and 88% yield. An asymetric Hydrogen auto-transfer process in the absence of an addnl. H donor gave the desired benzyl ketone in 92% ee. The reaction intermediate enone was detected by using in situ IR spectroscopy.
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