期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 12, 期 28, 页码 5102-5107出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ob01052c
关键词
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资金
- National Natural Science Foundation [21074004, 91227202]
- National Basic Research Program of the Ministry of Science and Technology of China [2013CB933500]
Unusual regio- and stereo-selectivity in Diels-Alder (D-A) reactions were achieved between bulky N-phenylmaleimides and anthracene derivatives. Using multiple substituents with steric hindrance on both diene and dienophile, a noticeable shift toward 1,4-addition was successfully obtained. The substrate scope in this reaction was broad and the highest yield of anti-1,4-adducts was over 90%. Novel structures of anti-1,4-adducts were confirmed by single crystal X-ray diffraction analysis. This study not only provides the first reported method of synthesizing anti-1,4-adducts and achieving otherwise unattainable regio-and stereo-selectivity, but also elucidates the importance of combining the steric effects of two reactants to shift products toward 1,4-adducts. Moreover, the resulting 1,4-adducts could be further functionalized through their halogen groups via carbon-carbon coupling reactions.
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