Development of Novel Carbon-Carbon Bond Forming Reactions by Allylic gem-Palladium/Metalloid Intermediates
| Project/Area Number |
15K05496
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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 | University of Toyama |
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Principal Investigator |
Horino Yoshikazu 富山大学, 大学院理工学研究部(工学), 准教授 (30447651)
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| Project Period (FY) |
2015-04-01 – 2018-03-31
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| Project Status |
Completed (Fiscal Year 2017)
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| Budget Amount *help |
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2017: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2016: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2015: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
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| Keywords | パラジウム / ホモアリルアルコール / アリル化反応 / 不斉転写 / アリルパラジウム / 三成分連結反応 / アリルボラン / アリルホウ素 / アリルスズ / カップリング反応 / ホウ素 / スズ |
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| Outline of Final Research Achievements |
In this research, we demonstrated the distinct reactivities of allylic gem-palladium/metalloid intermediates. For example, palladium-catalyzed three-component reaction of 3-(n-tributylstannyl)allyl acetates, aldehydes, and organoboranes afforded the (E)-anti-homoallylic alcohols with excellent diastereoselectivity and good to high levels of alkene stereocontrol. Moreover, we developed complementary reaction conditions to provide both (Z)- and (E)-homoallylic alcohols possessing aryl groups at the alkene terminus using a catalyst controlled strategy. The reaction showed good scope and functional group tolerance, many of which could pose difficulties for other transition-metal-catalyzed alkene isomerizations of alkenyl boronates. Thus, the catalytically generated allylic gem-palladium/boryl species promise to serve as synthetically useful intermediates.
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Report
(4 results)
Research Products
(45 results)
