TY - JOUR
T1 - Enantioselective Excited-State Nazarov Reaction
T2 - A Relay Strategy of Electrocyclization and Parallel Kinetic Resolution
AU - Qiao, Xuelong
AU - Xu, Jiwei
AU - He, Haibing
AU - Gao, Shuanhu
N1 - Publisher Copyright:
© 2024 American Chemical Society.
PY - 2024
Y1 - 2024
N2 - We report herein the enantioselective photoinduced Nazarov reaction using a relay strategy of an electrocyclization, followed by parallel kinetic resolution (PKR). No enantioselectivity was observed during electrocyclization due to weak coordination between chiral ligands and the substrate’s carbonyl group. However, PKR was successfully achieved in the deprotonation step with a bifunctional chiral thiourea ligand. Regioselective deprotonation, controlled by the chiral N,N-dimethyl amine motif, produced cis-6,5,6-fused tricyclic stereoisomers with high ee and yields.
AB - We report herein the enantioselective photoinduced Nazarov reaction using a relay strategy of an electrocyclization, followed by parallel kinetic resolution (PKR). No enantioselectivity was observed during electrocyclization due to weak coordination between chiral ligands and the substrate’s carbonyl group. However, PKR was successfully achieved in the deprotonation step with a bifunctional chiral thiourea ligand. Regioselective deprotonation, controlled by the chiral N,N-dimethyl amine motif, produced cis-6,5,6-fused tricyclic stereoisomers with high ee and yields.
UR - https://www.scopus.com/pages/publications/85211478871
U2 - 10.1021/acs.orglett.4c04177
DO - 10.1021/acs.orglett.4c04177
M3 - 文章
C2 - 39643589
AN - SCOPUS:85211478871
SN - 1523-7060
JO - Organic Letters
JF - Organic Letters
ER -