Department of Chemistry, The University of Kansas, Lawrence, Kansas 66045, USA.
Org Lett. 2010 Feb 19;12(4):740-2. doi: 10.1021/ol902828p.
Allyl nitroacetates undergo decarboxylative allylation to provide tertiary nitroalkanes in high yield. Moreover, the transformations are complete within several minutes under ambient conditions. High yields result because O-allylation of the intermediate nitronates, which is typically problematic, is reversible under conditions of the decarboxylative allylation process. Lastly, the preparation of substrate allyl nitroacetates by tandem Knoevenagel/Diels-Alder sequences allows the facile synthesis of relatively complex substrates that undergo diastereoselective decarboxylative allylation.
烯丙基硝基乙酸酯经脱羧烯丙基化反应以高收率得到叔硝基烷烃。此外,在环境条件下,这些转化在几分钟内即可完成。高收率的原因是中间硝翁盐的 O-烯丙基化,这通常是有问题的,但在脱羧烯丙基化过程的条件下是可逆的。最后,通过串联的 Knoevenagel/Diels-Alder 序列制备底物烯丙基硝基乙酸酯,可方便地合成相对复杂的底物,这些底物可进行非对映选择性脱羧烯丙基化反应。