Highly efficient photochemical addition of tertiary amines to electron deficient alkenes. Diastereoselective addition to (5R)-5-menthyloxy-2[5H]-furanone
作者:Samuel Bertrand、Cédric Glapski、Norbert Hoffmann、Jean-Pierre Pete
DOI:10.1016/s0040-4039(99)00451-7
日期:1999.4
efficiently (isolated yields up to 94%) to (5R)-5-mentyloxy-2[5H]-furanone. The addition, which follows a radical chain mechanism initiated by a photoinitiated electron transfer (PET) from the tertiary amine to the excited aromatic ketone, occurs with a complete facial selectivity on the furanone ring. The method can be generalized to the addition of tertiary amines and N-protected secondary amines to electron
衍生自吡咯烷的叔胺可以非常有效地(分离产率高达94%)添加到(5 R)-5-薄荷基氧基-2 [5 H ]-呋喃酮中。该加成遵循自由基链机理,该自由基链机理是由光引发的电子从叔胺转移至被激发的芳族酮而引发的,在呋喃酮环上具有完全的面部选择性。该方法可以推广到向缺电子的烯烃中添加叔胺和N-保护的仲胺。
Highly Efficient and Stereoselective Radical Addition of Tertiary Amines to Electron-Deficient Alkenes − Application to the Enantioselective Synthesis of Necine Bases
作者:Samuel Bertrand、Norbert Hoffmann、Jean-Pierre Pete