Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to 尾-Nitroolefins: Formal Synthesis of (S)-SKF 38393

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• 作者：Kung-Chih Huang ; Balraj Gopula ; Ting-Shen Kuo ; Chien-Wei Chiang ; Ping-Yu Wu ; Julian P. Henschke ; Hsyueh-Liang Wu
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：November 15, 2013
• 年：2013
• 卷：15
• 期：22
• 页码：5730-5733
• 全文大小：240K
• 年卷期：v.15,no.22(November 15, 2013)
• ISSN：1523-7052

文摘

An efficient enantioselective addition of an array of arylboronic acids to various 尾-nitrostyrenes catalyzed by a novel and reactive rhodium鈥揹iene catalyst (S/C up to 1000) was developed, providing 尾,尾-diarylnitroethanes in good to high yields (62鈥?9%) with excellent enantioselectivities (85鈥?7% ee). The method was extended to 2-heteroarylnitroolefins and 2-alkylnitroolefins similarly providing the desired products with high enantioselectivities and yields. The usefulness of this method was demonstrated in the formal synthesis of the enantiomer of the dopamine receptor agonist and antagonist, SKF 38393.