Development of New Chiral Phosphine Ligands with Helical Environments and Their Application in Asymmetric Catalytic Reactions
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- Usui Kazuteru
- Graduate School of Pharmaceutical Sciences, Kyushu University
Bibliographic Information
- Other Title
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- 螺旋空間を利用した新規不斉リン配位子の開発と不斉触媒反応への応用
- ラセン クウカン オ リヨウ シタ シンキ フセイ リン ハイイシ ノ カイハツ ト フセイ ショクバイ ハンノウ エ ノ オウヨウ
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Abstract
The design and development of new chiral ligands to enable precise stereocontrol in a wide variety of reactions is one of the most important branches of organic synthesis. To date, the development of hybrid ligands containing both σ-donating and π-donating groups has attracted considerable attention, with unprecedented reactivities and stereoselectivities being observed. Therefore to develop efficient hybrid chiral ligands with novel structural motifs, we envisage that helicene would be a suitable π-donor efficiently to construct a helical environment around a metal center. In this context, we herein describe our recent efforts to develop a series of novel chiral [5]helicene-derived phosphine ligands (L1, with a 7,8-dihydro[5]helicene core structure, and L2, with a fully aromatic [5]helicene core structure). The prepared ligands, and in particular L1, were found highly effective in the asymmetric allylation of 1,3-diphenylallyl acetate with indoles and etherification with alcohols. Furthermore, in the asymmetric Suzuki-Miyaura coupling reaction, L2 exhibited excellent enantioselectivities. Finally, density functional theory studies were employed to propose a model that accounts for the origin of such high enantioselectivity in these reactions.<br>
Journal
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- YAKUGAKU ZASSHI
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YAKUGAKU ZASSHI 137 (11), 1381-1390, 2017-11-01
The Pharmaceutical Society of Japan
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Details 詳細情報について
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- CRID
- 1390282681193921920
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- NII Article ID
- 130006191253
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- NII Book ID
- AN00284903
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- ISSN
- 13475231
- 00316903
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- NDL BIB ID
- 028622442
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- PubMed
- 29093375
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- Text Lang
- ja
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- Data Source
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
- KAKEN
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- Abstract License Flag
- Disallowed