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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.

Authors+Show Affiliations

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.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

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 -