期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 18, 期 22, 页码 6811-6824出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201103472
关键词
gold; homogeneous catalysis; ligand effects; propargyl acetates; stereoselectivity
资金
- Organic Chemistry Institute of the University of Zurich
- Legerlotz Stiftung
- Swiss National Science Foundation
The late transition metal catalyzed rearrangement of propargyl acetates offers an interesting platform for the development of synthetically useful transformations. We have recently shown that gold complexes can catalyze a highly selective tandem 1,2-/1,2-bis-acetoxy migration in 1,4-bis-propargyl acetates to form 2,3-bis-acetoxy-1,3-dienes. In this way, (1Z,3Z)- or (1Z,3E)- and (1E,3Z)-1,3-dienes could be obtained in a stereocontrolled manner depending on the electronic and steric features of the ancillary ligand bound to gold and the substituents at the propargylic positions. In this work, we report an experimental study on the scope of this transformation, plus a detailed theoretical examination of the reaction mechanism, which has revealed the key features responsible for the reaction stereoselectivity. Synthetic applications towards the one-pot synthesis of quinoxaline heterocycles and tandem DielsAlder processes have also been devised.
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