Efficient synthesis of optically active 4-nitro-cyclohexanones via bifunctional thiourea-base catalyzed double-Michael addition of nitromethane to dienones

Thiourea-modified cinchona alkaloids as bifunctional catalysts and a base could catalyze a stepwise [5+1] cyclization of divinyl ketones with nitromethane via double Michael additions, furnishing optically active 4-nitro-cyclohexanones with good yields, excellent diastereoselectivities (>20 : 1)...

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Veröffentlicht in:	Chemical communications (Cambridge, England) England), 2011-04, Vol.47 (13), p.3992-3994
Hauptverfasser:	Wu, Bin, Liu, Guo-Gui, Li, Mei-Qiu, Zhang, Yong, Zhang, Shao-Yun, Qiu, Jun-Ru, Xu, Xiao-Ping, Ji, Shun-Jun, Wang, Xing-Wang
Format:	Artikel
Sprache:	eng
Schlagworte:	Catalysis Cinchona Alkaloids - chemistry Cyclohexanones - chemical synthesis Cyclohexanones - chemistry Methane - analogs & derivatives Methane - chemistry Nitro Compounds - chemical synthesis Nitro Compounds - chemistry Nitroparaffins - chemistry Thiourea - chemistry
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Beschreibung
Zusammenfassung:	Thiourea-modified cinchona alkaloids as bifunctional catalysts and a base could catalyze a stepwise [5+1] cyclization of divinyl ketones with nitromethane via double Michael additions, furnishing optically active 4-nitro-cyclohexanones with good yields, excellent diastereoselectivities (>20 : 1) and high enantiomeric ratios (up to 97 : 3).
ISSN:	1359-7345 1364-548X
DOI:	10.1039/c0cc05418f