期刊
CHEMICAL SCIENCE
卷 9, 期 37, 页码 7327-7331出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8sc02103a
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资金
- JSPS KAKENHI [JP26288053]
- Uehara Memorial foundation
- Naito foundation
- Inoue Foundation of Science
Described herein is the BrOnsted acid-catalyzed double C(sp(3))-H bond functionalization of alkyl phenethyl ether derivatives. In this process, a [1,5]-[1,5]-hydride shift occurred successively to afford tricyclic fused pyran derivatives in excellent chemical yields with excellent diastereoselectivities (up to >20:1). The key to achieve this reaction was the introduction of two methyl groups at the benzylic position, which was effective in both hydride shift processes: (1) the Thorpe-Ingold effect for the first hydride shift and (2) conformational control in the second hydride shift.
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