書誌事項
- タイトル別名
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- Enantioselective Acid-Base Organocatalyzed Domino Reactions Based on aza-Morita-Baylis-Hillman Process
- サン-エンキガタ フセイ ユウキ ブンシ ショクバイ オ モチイル エナンチオ センタクテキ aza-モリタ-Baylis-Hillmanガタ ドミノ ハンノウ ノ カイハツ
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The aza-Morita-Baylis-Hillman (aza-MBH) reaction is a C-C bond-formation between enones and imines mediated by a nucleophilic Lewis base catalyst. The aza-MBH products are highly functionalized allylic amines which are proved to be valuable building blocks for pharmaceutical compounds. Organocatalyzed domino reactions are an attractive methodology because of its ability to construct complex chiral molecules from readily available substrates under mild reaction conditions in two or more steps in a single operation without using any toxic metals. However, a few reports on the domino reaction based on the MBH have been made due to the complicated MBH process involving Michael/Mannich/H-transfer/retro-Michael sequence. Herein, we report an enantioselective domino reaction based on the aza-MBH process using chiral acid-base organocatalysts. The acid-base functionalities activate the substrates and promote the complicated MBH sequence by their synergistic cooperation. The designed enantioselective MBH-type domino reactions provided highly functionalized heterocycles in up to 98% ee, some of which have a tetrasubstituted carbon stereogenic center.
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 72 (7), 781-796, 2014
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
- 1390282680316648064
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- NII論文ID
- 130004679609
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- NII書誌ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 025635348
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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