Journal
CHEMICAL COMMUNICATIONS
Volume 54, Issue 89, Pages 12650-12653Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8cc06390g
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Funding
- National Natural Science Foundation of China [21332003, 21772043]
- Guangdong Innovative and Entrepreneurial Research Team Program [2016ZT06Y337]
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A highly diastereoselective approach for the rapid construction of an isochroman skeleton was achieved by the copper(ii)-catalyzed transformation of alcohol-tethered enones and diazo compounds. This transformation was proposed to proceed through the intramolecular Michael-type trapping of an in situ generated oxonium ylide intermediate. The copper(ii) catalyst may play a dual role in catalyzing diazo decomposition as well as activating the enone unit. With this method, a series of 3,4-substituted isochromans were obtained with excellent diastereoselectivities under very mild reaction conditions.
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