Stereoselective Formation of Substituted 1,3-Dioxolanes through a Three-Component Assembly during the Oxidation of Alkenes with Hypervalent Iodine(III)

Molecules

Mio Shimogaki²  Morifumi Fujita¹  Takashi Sugimura²  Wesley Moran² 

[1] Graduate School of Material Science, University of Hyogo, Kohto, Kamigori, Hyogo 678-1297, Japan;

关键词: hypervalent iodine;    oxidation;    dioxolane;    dioxolanyl cation;    stereoselective synthesis;   

DOI  :  10.3390/molecules200917041

来源: mdpi

【 摘 要 】

Stereoselective formation of substituted 1,3-dioxolanes was achieved through an assembly of three components: alkene, carboxylic acid and silyl enol ether. The reaction proceeded via stereospecific generation of a 1,3-dioxolan-2-yl cation intermediate during oxidation of alkene substrates with hypervalent iodine. The stereoselective trapping of the cation intermediate with silyl enol ether completed the formation of the dioxolane product.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.