期刊
SYNTHESIS-STUTTGART
卷 46, 期 16, 页码 2149-2154出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0034-1378281
关键词
carbenoids; cyclization; heterocycles; homogeneous catalysis; regioselectivity; solvent effects
资金
- Zhejiang Provincial Natural Science Foundation [LY13B020007]
- National Natural Science Foundation of China [21002073, 21372178]
The solvent effect on the regiochemistry of the AuCl3-catalyzed cycloisomerization of a bromoallenyl ketone was evaluated by DFT calculations, which provided theoretical rationale for the original experimental findings from the Gevorgyan group. Upon the generation of the gold carbenoid intermediate from cyclization of the allene precursor, the tetrahydrofuran solvent could act as a proton shuttle to assist the 1,2-H migration to afford the 2-bromofuran product. This solvent-involved pathway is lower in energy than the 1,2-Br migration and thus leads to a solvent-controlled switch of regioselectivity in the reaction concerned.
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