Diastereo- and enantioselective rhodium(iii)-catalyzed reductive cyclization of cyclohexadienone-containing 1,6-dienes

Autor: Wen-Bo Ye, Ping Tian, Guo-Qiang Lin, Pei-Ying Peng, Dingding Gao, Ya-Jie Wang, Yun-Xuan Tan, Xi-Liang Liu
Rok vydání: 2021
Předmět:
Zdroj: Chemical Communications. 57:9724-9727
ISSN: 1364-548X
1359-7345
DOI: 10.1039/d1cc03645a
Popis: A diastereo- and enantioselective rhodium(III)-catalyzed reductive cyclization of cyclohexadienone-tethered terminal alkenes and (E)-1,2-disubstituted alkenes (1,6-dienes) is reported, providing cis-bicyclic products bearing three contiguous stereocenters with good yields and high diastereo- and enantioselectivities. The kinetic resolution of the racemic precursor is also achieved with good efficiency. Moreover, a subgram-scale experiment, several transformations of the cyclization product, and one-pot preparation of bridged polycyclic frameworks are presented.
Databáze: OpenAIRE