Copper-Catalyzed Asymmetric Diyne Cyclization via [1,2]-Stevens-Type Rearrangement for the Synthesis of Chiral Chromeno[3,4-c]pyrroles

Autor: Feng‐Lin Hong, Chong‐Yang Shi, Pan Hong, Tong‐Yi Zhai, Xin‐Qi Zhu, Xin Lu, Long‐Wu Ye
Rok vydání: 2021
Předmět:
Zdroj: Angewandte Chemie (International ed. in English). 61(7)
ISSN: 1521-3773
Popis: Here, we report a copper-catalyzed asymmetric cascade cyclization/[1,2]-Stevens-type rearrangement via a non-diazo approach, leading to the practical and atom-economic assembly of various valuable chiral chromeno[3,4-c]pyrroles bearing a quaternary carbon stereocenter in generally moderate to good yields with wide substrate scope and excellent enantioselectivities (up to 99 % ee). Importantly, this protocol not only represents the first example of catalytic asymmetric [1,2]-Stevens-type rearrangement based on alkynes but also constitutes the first asymmetric formal carbene insertion into the Si-O bond.
Databáze: OpenAIRE