期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 352, 期 17, 页码 2966-2978出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201000079
关键词
cyclophanes; cyclopropanes; enantioselectivity; heterocycles; planar chirality; ylides
资金
- JSPS [19550112]
- Grants-in-Aid for Scientific Research [19550112] Funding Source: KAKEN
Novel planar-chiral pyridinium ylides were designed, and generated in situ from the corresponding pyridinium salts with triethylamine. Ylides with a common parapyridinophane skeleton reacted efficiently with electron-deficient dicyanoalkenes, or malononitriles, to produce optically active cyclopropane derivatives with high enantioselectivity (up to 99% ee). Remote steric effects were observed on the enantioselectivities, where the R-2 groups of the pyridinophane core resulted in higher ee values of the products. Density function theory (DFT) calculations are in good agreement with our experimental results: the energetically favored transition state leads to the major stereoisomer, namely the trans-cyclopropane products.
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