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Highly enantioselective [3 + 2]-annulation of isatin-derived morita-baylis-hillman adducts with cyclic sulfonimines.
Org Lett. 2015 Apr 03; 17(7):1688-91.OL

Abstract

An organocatalytic [3 + 2]-annulation between isatin-derived Morita-Baylis-Hillman adducts and cyclic sulfonimines has been developed in high yields with excellent enantio- and diastereoselectivities via an allylic nitrogen-ylide intermediate. The reaction provides access to heavily substituted aza-spirooxindole derivatives, which also contain ring fused cyclic sultams.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Wei F
Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China. University of Chinese Academy of Sciences, Beijing 100049, China.
Huang HY
Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China. University of Chinese Academy of Sciences, Beijing 100049, China.
Zhong NJ
Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China. University of Chinese Academy of Sciences, Beijing 100049, China.
Gu CL
Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China. University of Chinese Academy of Sciences, Beijing 100049, China.
Wang D
Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China. University of Chinese Academy of Sciences, Beijing 100049, China.
Liu L
Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China. University of Chinese Academy of Sciences, Beijing 100049, China.

MeSH

CatalysisIsatinMolecular StructureStereoisomerismSulfhydryl Compounds

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

25781216

Citation

Wei, Feng, et al. "Highly Enantioselective [3 + 2]-annulation of Isatin-derived Morita-baylis-hillman Adducts With Cyclic Sulfonimines." Organic Letters, vol. 17, no. 7, 2015, pp. 1688-91.
Wei F, Huang HY, Zhong NJ, et al. Highly enantioselective [3 + 2]-annulation of isatin-derived morita-baylis-hillman adducts with cyclic sulfonimines. Org Lett. 2015;17(7):1688-91.
Wei, F., Huang, H. Y., Zhong, N. J., Gu, C. L., Wang, D., & Liu, L. (2015). Highly enantioselective [3 + 2]-annulation of isatin-derived morita-baylis-hillman adducts with cyclic sulfonimines. Organic Letters, 17(7), 1688-91. https://doi.org/10.1021/acs.orglett.5b00456
Wei F, et al. Highly Enantioselective [3 + 2]-annulation of Isatin-derived Morita-baylis-hillman Adducts With Cyclic Sulfonimines. Org Lett. 2015 Apr 3;17(7):1688-91. PubMed PMID: 25781216.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly enantioselective [3 + 2]-annulation of isatin-derived morita-baylis-hillman adducts with cyclic sulfonimines. AU - Wei,Feng, AU - Huang,Hong-Yan, AU - Zhong,Neng-Jun, AU - Gu,Chun-Ling, AU - Wang,Dong, AU - Liu,Li, Y1 - 2015/03/17/ PY - 2015/3/18/entrez PY - 2015/3/18/pubmed PY - 2015/10/20/medline SP - 1688 EP - 91 JF - Organic letters JO - Org Lett VL - 17 IS - 7 N2 - An organocatalytic [3 + 2]-annulation between isatin-derived Morita-Baylis-Hillman adducts and cyclic sulfonimines has been developed in high yields with excellent enantio- and diastereoselectivities via an allylic nitrogen-ylide intermediate. The reaction provides access to heavily substituted aza-spirooxindole derivatives, which also contain ring fused cyclic sultams. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/25781216/Highly_enantioselective_[3_+_2]_annulation_of_isatin_derived_morita_baylis_hillman_adducts_with_cyclic_sulfonimines_ DB - PRIME DP - Unbound Medicine ER -