キラルなロジウム(II)錯体を用いるα-ジアゾエステルの分子内C-H挿入反応：1,2-二置換シクロペンタン誘導体の触媒的不斉合成
書誌事項
- タイトル別名
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- Intramolecular C-H Insertion Reaction of α-Diazoesters Catalyzed by Chiral Dirhodium(II) Carboxylates: Enantio- and Diastereoselective Construction of 1,2-Disubstituted Cyclopentane Compounds
- 公開日
- 2005
- DOI
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- 10.14895/hannou.31.0.184.0
- 公開者
- 日本薬学会化学系薬学部会
説明
A highly enantio- and diastereoselective intramolecular C-H insertion reaction of α-diazoesters has been achieved with the use of dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate] as a catalyst, providing exclusively cis-2-arylcyclopentane-1-carboxylates in up to 95% ee with no evidence of alkene formation. As expected from the robust nature and high reactivity, 0.05 mol % of Rh2(S-PTTL)4 was found to catalyze the reaction of methyl 2-diazo-6-phenylhexanoate without compromising either the yield or enantioselectivity. Rh2(S-PTTL)4 was also found to catalyze the C-H insertion reaction of α-diazoester containing a benzene ring on the tether to give methyl cis-2,3-dihydro-1-phenyl-1H-indene-2-carboxylate in 92% ee. The present catalytic protocol provides attractive and powerful access to optically active cyclopentane building brocks.
収録刊行物
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- 反応と合成の進歩シンポジウム 発表要旨概要
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反応と合成の進歩シンポジウム 発表要旨概要 31 (0), 184-184, 2005
日本薬学会化学系薬学部会
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詳細情報 詳細情報について
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- CRID
- 1390282680611359232
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- NII論文ID
- 130006997084
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- データソース種別
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- JaLC
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可