期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 42, 页码 13210-13214出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201608087
关键词
alkenes; catalysis; cross-metathesis; enoates; molybdenum
资金
- NIH [GM-59426]
Kinetically controlled catalytic cross-metathesis reactions that generate (Z)-alpha, beta-unsaturated esters selectively are disclosed. A key finding is that the presence of acetonitrile obviates the need for using excess amounts of a more valuable terminal alkene substrates. On the basis of X-ray structure and spectroscopic investigations a rationale for the positive impact of acetonitrile is provided. Transformations leading to various E,Z-dienoates are highly Z-selective as well. Utility is highlighted by application to stereoselective synthesis of the C1-C12 fragment of biologically active natural product (-)-laulimalide.
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