Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 45, Pages 16252-16259Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201908495
Keywords
asymmetric catalysis; cyclizations; desymmetrization; heterocycles; organocatalysis
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Funding
- National Natural Science Foundation of China [21622204, 91545105, 21772161]
- Xiamen University [20720180036]
- NFFTBS [J1310024]
- PCSIRT
- Science & Technology Cooperation Program of Xiamen [3502Z20183015]
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Described herein is an organocatalytic enantioselective desymmetrizing cycloisomerization of arylsulfonyl-protected ynamide cyclohexanones, representing the first metal-free asymmetric Conia-ene-type carbocyclization. This method allows the highly efficient and atom-economical construction of a range of valuable morphans with wide substrate scope and excellent enantioselectivity (up to 97 % ee). In addition, such a cycloisomerization of alkylsulfonyl-protected ynamide cyclohexanones can lead to the divergent synthesis of normorphans as the main products with high enantioselectivity (up to 90 % ee). Moreover, theoretical calculations are employed to elucidate the origins of regioselectivity and enantioselectivity.
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