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Tertiary amine-catalyzed chemoselective and asymmetric [3 + 2] annulation of Morita-Baylis-Hillman carbonates of isatins with propargyl sulfones.
Org Lett. 2011 Sep 02; 13(17):4584-7.OL

Abstract

A chemo- and enantioselective [3 + 2] annulation of Morita-Baylis-Hillman carbonates of isatins with propargyl sulfones was catalyzed by a β-ICD O-MOM ether 1c, affording spirocyclic 2-oxindoles bearing an unusual cyclopentadiene motif in outstanding ee values (up to >99%). More electrophiles, such as N-phenylmaleimide, have been also utilized to deliver complex spirocyclic 2-oxindoles with good results.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Peng J
Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Huang X
No affiliation info available
Jiang L
No affiliation info available
Cui HL
No affiliation info available
Chen YC
No affiliation info available

MeSH

AlkynesAminesCarbonatesCatalysisIsatinMolecular StructureStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

21815615

Citation

Peng, Jing, et al. "Tertiary Amine-catalyzed Chemoselective and Asymmetric [3 + 2] Annulation of Morita-Baylis-Hillman Carbonates of Isatins With Propargyl Sulfones." Organic Letters, vol. 13, no. 17, 2011, pp. 4584-7.
Peng J, Huang X, Jiang L, et al. Tertiary amine-catalyzed chemoselective and asymmetric [3 + 2] annulation of Morita-Baylis-Hillman carbonates of isatins with propargyl sulfones. Org Lett. 2011;13(17):4584-7.
Peng, J., Huang, X., Jiang, L., Cui, H. L., & Chen, Y. C. (2011). Tertiary amine-catalyzed chemoselective and asymmetric [3 + 2] annulation of Morita-Baylis-Hillman carbonates of isatins with propargyl sulfones. Organic Letters, 13(17), 4584-7. https://doi.org/10.1021/ol201776h
Peng J, et al. Tertiary Amine-catalyzed Chemoselective and Asymmetric [3 + 2] Annulation of Morita-Baylis-Hillman Carbonates of Isatins With Propargyl Sulfones. Org Lett. 2011 Sep 2;13(17):4584-7. PubMed PMID: 21815615.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Tertiary amine-catalyzed chemoselective and asymmetric [3 + 2] annulation of Morita-Baylis-Hillman carbonates of isatins with propargyl sulfones. AU - Peng,Jing, AU - Huang,Xin, AU - Jiang,Lin, AU - Cui,Hai-Lei, AU - Chen,Ying-Chun, Y1 - 2011/08/04/ PY - 2011/8/6/entrez PY - 2011/8/6/pubmed PY - 2011/12/13/medline SP - 4584 EP - 7 JF - Organic letters JO - Org Lett VL - 13 IS - 17 N2 - A chemo- and enantioselective [3 + 2] annulation of Morita-Baylis-Hillman carbonates of isatins with propargyl sulfones was catalyzed by a β-ICD O-MOM ether 1c, affording spirocyclic 2-oxindoles bearing an unusual cyclopentadiene motif in outstanding ee values (up to >99%). More electrophiles, such as N-phenylmaleimide, have been also utilized to deliver complex spirocyclic 2-oxindoles with good results. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/21815615/Tertiary_amine_catalyzed_chemoselective_and_asymmetric_[3_+_2]_annulation_of_Morita_Baylis_Hillman_carbonates_of_isatins_with_propargyl_sulfones_ L2 - https://doi.org/10.1021/ol201776h DB - PRIME DP - Unbound Medicine ER -