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One-pot tandem approach to spirocyclic oxindoles featuring adjacent spiro-stereocenters.
Angew Chem Int Ed Engl. 2013 Dec 16; 52(51):13735-9.AC

Abstract

All in a sequence: An organocatalyzed Morita-Baylis-Hillman (MBH)/bromination/[3+2] annulation sequence for highly stereoselective syntheses of bis(spirooxindole)s featuring adjacent spiro-stereocenters is described. The key step is an unprecedented catalytic asymmetric [3+2] annulation of isatin-derived MBH adducts, containing a tetrasubstituted alkene moiety, with isatins.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Liu YL
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China).
Wang X
No affiliation info available
Zhao YL
No affiliation info available
Zhu F
No affiliation info available
Zeng XP
No affiliation info available
Chen L
No affiliation info available
Wang CH
No affiliation info available
Zhao XL
No affiliation info available
Zhou J
No affiliation info available

MeSH

CatalysisIndolesMolecular StructureOxindolesSpiro CompoundsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

24346948

Citation

Liu, Yun-Lin, et al. "One-pot Tandem Approach to Spirocyclic Oxindoles Featuring Adjacent Spiro-stereocenters." Angewandte Chemie (International Ed. in English), vol. 52, no. 51, 2013, pp. 13735-9.
Liu YL, Wang X, Zhao YL, et al. One-pot tandem approach to spirocyclic oxindoles featuring adjacent spiro-stereocenters. Angew Chem Int Ed Engl. 2013;52(51):13735-9.
Liu, Y. L., Wang, X., Zhao, Y. L., Zhu, F., Zeng, X. P., Chen, L., Wang, C. H., Zhao, X. L., & Zhou, J. (2013). One-pot tandem approach to spirocyclic oxindoles featuring adjacent spiro-stereocenters. Angewandte Chemie (International Ed. in English), 52(51), 13735-9. https://doi.org/10.1002/anie.201307250
Liu YL, et al. One-pot Tandem Approach to Spirocyclic Oxindoles Featuring Adjacent Spiro-stereocenters. Angew Chem Int Ed Engl. 2013 Dec 16;52(51):13735-9. PubMed PMID: 24346948.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - One-pot tandem approach to spirocyclic oxindoles featuring adjacent spiro-stereocenters. AU - Liu,Yun-Lin, AU - Wang,Xin, AU - Zhao,Yu-Lei, AU - Zhu,Feng, AU - Zeng,Xing-Ping, AU - Chen,Long, AU - Wang,Cui-Hong, AU - Zhao,Xiao-Li, AU - Zhou,Jian, Y1 - 2013/11/07/ PY - 2013/08/18/received PY - 2013/09/27/revised PY - 2013/12/19/entrez PY - 2013/12/19/pubmed PY - 2014/11/5/medline KW - asymmetric catalysis KW - heterocycles KW - organocatalysis KW - spiro compounds KW - synthetic methods SP - 13735 EP - 9 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 52 IS - 51 N2 - All in a sequence: An organocatalyzed Morita-Baylis-Hillman (MBH)/bromination/[3+2] annulation sequence for highly stereoselective syntheses of bis(spirooxindole)s featuring adjacent spiro-stereocenters is described. The key step is an unprecedented catalytic asymmetric [3+2] annulation of isatin-derived MBH adducts, containing a tetrasubstituted alkene moiety, with isatins. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/24346948/One_pot_tandem_approach_to_spirocyclic_oxindoles_featuring_adjacent_spiro_stereocenters_ DB - PRIME DP - Unbound Medicine ER -