Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 23, Pages 11759-11767Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo5022037
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Funding
- National Natural Science Foundation of China [21002022, 21442007]
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Asymmetric alkynylation of seven-membered cyclic imine dibenzo[b,f][1,4]oxazepines is successfully achieved by combining chiral phosphoric acid and Ag(I) catalysts. Various arylacetylenes, conjugated enynes, and terminal 1,3-diynes are good substrates for this reaction, and aliphatic hexyne is also a suitable donor at elevated temperature. Optimization of this approach has provided a facile method to synthesize optically active 11-substituted-10,11-dihydrodibenzo[b,f][1,4]oxazepine derivatives containing a carbon-carbon triple bond with 63-99% ee. Subsequent transformations of the carbon-carbon triple bond for the heterocyclic products have been disclosed.
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