A new protocol for the in situ generation of aromatic, heteroaromatic, and unsaturated diazo compounds and its application in catalytic and asymmetric epoxidation of …

…, M Patel, M Porcelloni, J Richardson…

Index: Aggarwal, Varinder K.; Alonso, Emma; Bae, Imhyuck; Hynd, George; Lydon, Kevin M.; Palmer, Matthew J.; Patel, Mamta; Porcelloni, Marina; Richardson, Jeffery; Stenson, Rachel A.; Studley, John R.; Vasse, Jean-Luc; Winn, Caroline L. Journal of the American Chemical Society, 2003 , vol. 125, # 36 p. 10926 - 10940

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Citation Number: 156

Abstract

A variety of metalated tosylhydrazone salts derived from benzaldehyde have been prepared and were reacted with benzaldehyde in the presence of tetrahydrothiophene (THT)(20 mol%) and Rh2 (OAc) 4 (1 mol%) to give stilbene oxide. Of the lithium, sodium, and potassium salts tested, the sodium salt was found to give the highest yield and selectivity. This study was extended to a wide variety of aromatic, heteroaromatic, aliphatic, α, β- ...