書誌事項
- タイトル別名
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- Catalytic Asymmetric Synthesis with Chirality-Switchable Helical Polymer Ligands
- キラリティースイッチング オ トクチョウ ト スル ラセン コウブンシ ハイイシ オ モチイタ ショクバイテキ フセイ ゴウセイ
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Polyquinoxaline-based helically chiral phosphine ligands PQXphos, bearing chiral side chains, were synthesized via living aromatizing copolymerization of o-diisocyanobenzene monomers. The chiral reaction environment of PQXphos is created on the basis of its single-handed helical structure, leading to high enantioselectivities in palladium-catalyzed asymmetric hydrosilylation of styrenes (up to 98% ee), Suzuki-Miyaura coupling (up to 98% ee), and silaborative C-C cleavage of meso-methylenecyclopropanes (up to 97% ee). While most common organic solvents induce right-handed helix to (R)-PQXphos bearing (R)-2-butoxymethyl side chains, 1,1,2-trichloroethane and some solvents induce left-handed helix to it. The inverted, left-handed (R)-PQXphos also showed high enantioselectivities for the production of enantiomers of the products obtained with right-handed (R)-PQXphos. PQXphos formed insoluble polymer complex through coordination to palladium. The insoluble palladium complex of PQXphos was reused 8 times, while keeping catalyst activity and enantioselectivity. In the silaborative desymmetrization of methylenecyclopropanes, PQXphos showed not only high enantioselectivity, but also high catalyst activity in comparison with the corresponding low-molecular-weight ligand.
収録刊行物
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- 有機合成化学協会誌
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有機合成化学協会誌 71 (5), 461-471, 2013
公益社団法人 有機合成化学協会
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詳細情報 詳細情報について
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- CRID
- 1390001205341601920
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- NII論文ID
- 10031171537
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- NII書誌ID
- AN0024521X
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- COI
- 1:CAS:528:DC%2BC3sXosVOrtrg%3D
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 024663845
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- 本文言語コード
- ja
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- データソース種別
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- JaLC
- NDL
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- 使用不可