Journal
CHEMICAL COMMUNICATIONS
Volume 50, Issue 17, Pages 2161-2163Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3cc48606k
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Funding
- National Natural Science Foundation of China [21021001, 21172151]
- Ministry of Education [20110181130014]
- National Basic Research Program of China (973 Program) [2010CB833300]
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A novel and efficient N, N'-dioxide-Gd(III) complex was developed for the highly diastereo- and enantioselective [3+2] cycloaddition of aryl oxiranyl diketones and aldehydes via C-C bond cleavage of oxiranes. The corresponding chiral 1,3-dioxolanes were obtained in excellent yields (up to 99%) with high diastereoselectivities (>95:5 dr) and enantioselectivities (up to 91% ee). Moreover, a possible transition model was proposed to explain the origin of the asymmetric induction.
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