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J Am Chem Soc

Title:		"Asymmetric organocatalytic epoxidation of alpha,beta-unsaturated aldehydes with hydrogen peroxide"
Author(s):		Marigo M; Franzen J; Poulsen TB; Zhuang W; Jorgensen KA;
Address:		"Danish National Research Foundation, Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark"
Journal Title:		J Am Chem Soc
Year:		2005
Volume:		127
Issue:		19
Page Number:		6964 - 6965
DOI:		10.1021/ja051808s
ISSN/ISBN:		0002-7863 (Print) 0002-7863 (Linking)
Abstract:		"The first asymmetric organocatalytic epoxidation of alpha,beta-unsaturated aldehydes is presented. A chiral bisaryl-silyl-protected pyrrolidine acts as a very selective epoxidation organocatalyst using simple oxidation agents, such as hydrogen peroxide and tert-butyl hydroperoxide. The asymmetric epoxidation reactions proceed under environmental friendly reaction condition in, for example, water mixtures of alcohols, and the scope of the reaction is demonstrated by the formation of optically active alpha,beta-epoxy aldehydes in high yields and enantioselectivities >94% ee. Furthermore, the direct synthesis of the sex pheromone from an acaric mite by asymmetric epoxidation of citral is presented"
Keywords:
Notes:		"PubMed-not-MEDLINEMarigo, Mauro Franzen, Johan Poulsen, Thomas B Zhuang, Wei Jorgensen, Karl Anker eng 2005/05/12 J Am Chem Soc. 2005 May 18; 127(19):6964-5. doi: 10.1021/ja051808s"