Development of Catalytic Asymmetric Reactions Focussing on Fluoroorganic Compounds.
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- Iseki Katsuhiko
- Chemical Division, Daikin Industries, Ltd.
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Highly enantioselective catalyses for preparing α, α-difluoro-β-hydroxycarboxylates and secondary α-trifluoromethyl alcohols have been developed. Difluoroketene ethyl trimethylsilyl acetal reacts with aldehydes in the presence of chiral boron complexes to afford the aldol adducts with up to 98% ee. The hydrogenation of 1, 1, 1-trifluoroalkan-2-one enol acetates using chiral ruthenium catalysts provides the secondary α-trifluoromethyl alcohols of excellent enantiopurity. The trifluoromethylation of carbonyl compounds with TMSCF3catalyzed by chiral quaternary ammonium fluorides or triaminosulfonium salts was assessed for synthesizing optically active α-trifluoromethyl alcohols including the tertiary alcohols which, unfortunately, gave moderate enantioselection. Throughout the course of our search for asymmetric catalysts for the trifluoromethylation, two types of Lewis bases, chiral phosphoramides and formamides, have been newly synthesized, and their successful application to the allylation of aldehydes with allylic trichlorosilanes is also described, which provide the corresponding homoallylic alcohols with good-to-excellent enantioselectivity.
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 58 (11), 1037-1047, 2000
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
- 1390282680255546624
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- NII論文ID
- 10008821995
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- NII書誌ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 5549663
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- NDL
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