An Atom-Economic Synthesis of Bicyclo[3.1.0]hexanes by Rhodium N-Heterocyclic Carbene-Catalyzed Diastereoselective Tandem Hetero-[5 2] Cycloaddition/Claisen Rearrangement Reaction of Vinylic Oxiranes with Alkynes

作者：Feng, Jian Jun; Zhang, Junliang^*

来源：Journal of the American Chemical Society, 2011, 133(19): 7304-7307.

DOI：10.1021/ja2014604

• Atom economic
• Bicyclic products
• Cycloaddition reaction
• Diastereoselective
• N-heterocyclic carbenes
• Rearrangement reactions
• Regiospecific
• Synthetic application

The first synthetic application of a vinylic oxirane as a heteroatom-containing five-atom component in transition-metal-catalyzed cycloaddition reactions is reported. A new, efficient, diastereoselective tandem intramolecular hetero-[5 2] cycloaddition/Claisen rearrangement of vinylic oxirane-alkyne substrates that uses a rhodium NHC complex and provides strategically novel, atom-economic, regiospecific, and diastereoselective access to [3.1.0] bicyclic products has been developed.

• 出版日期2011-5-18
• 单位华东师范大学