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Pd(II)-Catalyzed Asymmetric Addition of Arylboronic Acids to Isatin-Derived Ketimines.
Org Lett. 2016 Jan 15; 18(2):288-91.OL

Abstract

A Pd(II)/Pyrox-catalyzed enantioselecitve addition of arylboronic acids to 3-ketimino oxindoles was developed, providing chiral 3-amino-2-oxindoles with a quaternary stereocenter in high yields and with good enantioselectivities. A variety of functionalized 3-ketimino oxindoles can be used, and the method tolerates some variation in arylboronic acid scope. This asymmetric arylation provides an alternative efficient catalytic method for the preparation of chiral 3-aryl-3-amino-2-oxindoles, which also represents the first example of a Pd(II)-catalyzed addition of arylborons to exocyclic ketimines.

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Publisher Full Text (DOI)

Authors+Show Affiliations

He Q
School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University , 800 Dongchuan Road, Shanghai 200240, China.
Wu L
School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University , 800 Dongchuan Road, Shanghai 200240, China.
Kou X
School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University , 800 Dongchuan Road, Shanghai 200240, China.
Butt N
School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University , 800 Dongchuan Road, Shanghai 200240, China.
Yang G
School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University , 800 Dongchuan Road, Shanghai 200240, China.
Zhang W
School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University , 800 Dongchuan Road, Shanghai 200240, China.

MeSH

Boronic AcidsCatalysisIminesIndolesIsatinMolecular StructureNitrilesOxindolesPalladiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

26720106

Citation

He, Qun, et al. "Pd(II)-Catalyzed Asymmetric Addition of Arylboronic Acids to Isatin-Derived Ketimines." Organic Letters, vol. 18, no. 2, 2016, pp. 288-91.
He Q, Wu L, Kou X, et al. Pd(II)-Catalyzed Asymmetric Addition of Arylboronic Acids to Isatin-Derived Ketimines. Org Lett. 2016;18(2):288-91.
He, Q., Wu, L., Kou, X., Butt, N., Yang, G., & Zhang, W. (2016). Pd(II)-Catalyzed Asymmetric Addition of Arylboronic Acids to Isatin-Derived Ketimines. Organic Letters, 18(2), 288-91. https://doi.org/10.1021/acs.orglett.5b03458
He Q, et al. Pd(II)-Catalyzed Asymmetric Addition of Arylboronic Acids to Isatin-Derived Ketimines. Org Lett. 2016 Jan 15;18(2):288-91. PubMed PMID: 26720106.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Pd(II)-Catalyzed Asymmetric Addition of Arylboronic Acids to Isatin-Derived Ketimines. AU - He,Qun, AU - Wu,Liang, AU - Kou,Xuezhen, AU - Butt,Nicholas, AU - Yang,Guoqiang, AU - Zhang,Wanbin, Y1 - 2015/12/31/ PY - 2016/1/1/entrez PY - 2016/1/1/pubmed PY - 2016/6/4/medline SP - 288 EP - 91 JF - Organic letters JO - Org Lett VL - 18 IS - 2 N2 - A Pd(II)/Pyrox-catalyzed enantioselecitve addition of arylboronic acids to 3-ketimino oxindoles was developed, providing chiral 3-amino-2-oxindoles with a quaternary stereocenter in high yields and with good enantioselectivities. A variety of functionalized 3-ketimino oxindoles can be used, and the method tolerates some variation in arylboronic acid scope. This asymmetric arylation provides an alternative efficient catalytic method for the preparation of chiral 3-aryl-3-amino-2-oxindoles, which also represents the first example of a Pd(II)-catalyzed addition of arylborons to exocyclic ketimines. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/26720106/Pd_II__Catalyzed_Asymmetric_Addition_of_Arylboronic_Acids_to_Isatin_Derived_Ketimines_ DB - PRIME DP - Unbound Medicine ER -