Journal
TETRAHEDRON
Volume 89, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2021.132163
Keywords
Asymmetric organocatalysis; Allylic alkylation-lactamization; Morita-Baylis-Hillman carbonates; Spirooxindole
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Funding
- National Natural Science Foundation of China [21576296, 21776318, 81703365, 22003077]
- Natural Science Foundation of Hunan Province [2018JJ3868, 2017JJ3401]
- Central South University
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A new synthetic method has been developed for the efficient synthesis of chiral spirocyclic oxindole-alpha-methylene-gamma-lactams. The method utilizes Morita-Baylis-Hillman carbonates as substrates and quinidine derivatives as catalysts to achieve stereoselective control over the products. This research broadens the application of Morita-Baylis-Hillman carbonates in the asymmetric construction of spirocyclic oxindoles.
An asymmetric allylic alkylation-lactamization domino sequence of 3-aminooxindoles with Morita-Baylis-Hillman carbonates catalyzed by quinidine derivative (beta-ICD) was developed. And a series of chiral spirocyclic oxindole-alpha-methylene-gamma-lactams have been facilely prepared in good yields and stereoselectivities. This developed protocol would broaden the utilization of Morita-Baylis-Hillman carbonates in asymmetric construction of spirocyclic oxindoles. (C) 2021 Elsevier Ltd. All rights reserved.
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