期刊
CHEMICAL SCIENCE
卷 8, 期 8, 页码 5699-5704出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7sc02176c
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资金
- National University of Singapore [R-143-000-599-112]
- National Natural Science Foundation of China [21672158]
- China Scholarship Council
- KFUPM-NUS Collaborative Fund [NUS15103NUS15103, R-143-004-617-597]
Catalyst-controlled regiodivergent [3 + 2] annulations of aurones and allenoates have been developed. When a dipeptide phosphine catalyst with an L-D-configuration was employed, a-selective [3 + 2] annulation products could be obtained with good regioselectivities and enantioselectivities. With the employment of L-L-dipeptide phosphines, g-selective annulation products could be selectively obtained with excellent enantioselectivities. By simply tuning the catalyst configurations, a wide range of alpha-selective or g-selective spirocyclic benzofuranones with either aryl or alkyl substitutions could be readily prepared. DFT calculations suggest that the conformation of the dipeptide phosphines influences the hydrogen bonding interactions or the distortion energy, resulting in delicate energy differentiation in the transition states, and accounting for the observed regioselectivity.
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