Gold-Catalyzed Reactivity Reversal of Indolizidinone-Tethered β‑Amino Allenes Controlled by the Stereochemistry

The controllable cyclization reaction
of indolizidinone-tethered
β-amino allenes has been achieved through gold catalysis. The
expected cycloisomerization of the syn-isomer sharply
contrasts to the unprecedented bis­(azacyclization)–spirocyclization
sequence of the epimeric anti-isomer, offering highly
selective access to enantiopure fused and spiranic azapolycycles.

通过金催化，成功实现了吲哚里西啶酮连接的β-氨基联烯的可控环化反应。顺式异构体仅发生预期的环异构化反应，其与差向异构的反式异构体所经历的前所未有的双氮杂环化-螺环化序列形成鲜明对比，该方法可为对映纯的稠合型与螺环型氮杂多环化合物提供高选择性的合成途径。