科研之友
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摘要
A new and efficient method of the synthesis of tributyl--keto- and tributyl--alkoxycarbonylalkylidenephosphorane via treatment of tributyl[(trimethylsilyl)- methylene]phosphorane with acid chlorides or chloroformate is described. These compounds have been studied less often than their triphenyl analogues (Maryanoff and Reitz, Chem Rev 1989, 89, 870; Taillefer and Cristau, Top Curr Chem, 2003, 229, 41; Appel, Loos, and Mayr, J Am Chem Soc 2009, 131, 704) because trialkyl-stabilized ylides are very reactive, highly perishable, and more difficult to synthesize. This paper also presents the reaction of in situ generated tributyl--keto- and tributyl--alkoxycarbonylalkylidenephosphoranes with p-nitrobenzaldehyde as a model aldehyde to obtain ,-unsaturated ketones and esters. All reactions result in Wittig products in a completely E-stereoselective manner.
- 出版日期2015-5
