A New Family of Cinchona-Derived Bifunctional Asymmetric Phase-Transfer Catalysts: Application to the Enantio- and Diastereoselective Nitro-Mannich Reaction of Amidosulfones

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• 作者：Kayli M. Johnson ; Matt S. Rattley ; Filippo Sladojevich ; David M. Barber ; Marta G. Nu帽ez ; Anna M. Goldys ; Darren J. Dixon
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：May 18, 2012
• 年：2012
• 卷：14
• 期：10
• 页码：2492-2495
• 全文大小：257K
• 年卷期：v.14,no.10(May 18, 2012)
• ISSN：1523-7052

文摘

A new family of bifunctional H-bond donor phase-transfer catalysts derived from cinchona alkaloids has been developed and evaluated in the enantio- and diastereoselective nitro-Mannich reaction of in situ generated N-Boc-protected imines of aliphatic, aromatic, and heteroaromatic aldehydes. Under optimal conditions, good reactivity and high diastereoselectivities (up to 24:1 dr) and enantioselectivities (up to 95% ee) were obtained using a 9-amino-9-deoxyepiquinidine-derived phase-transfer catalyst possessing a 3,5-bis(trifluoromethyl)phenylurea H-bond donor group at the 9-position.