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Highly enantioselective synthesis of 3-amino-2-oxindole derivatives: catalytic asymmetric alpha-amination of 3-substituted 2-oxindoles with a chiral scandium complex.
Chemistry. 2010 Jun 11; 16(22):6632-7.C

Abstract

A highly enantioselective alpha-amination of 3-substituted oxindoles with azodicarboxylates catalyzed by a chiral Sc(OTf)(3)/N,N'-dioxide complex (Tf: triflate) has been developed and affords the corresponding 3-amino-2-oxindole derivatives in high yields (up to 98%) with excellent enantioselectivities (up to 99% ee). The procedure is capable of tolerating a relatively wide range of substrates, and excellent results (92-96% ee) can also be obtained, even in the presence of 0.5 mol % of catalyst loading under mild conditions. These results showed the potential value of the catalytic approach. Moreover, with high synthetic versatility, the product could be easily transformed into optically active 3-amino-3-methyloxindole bearing a chiral quaternary stereogenic center.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Yang Z
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China.
Wang Z
No affiliation info available
Bai S
No affiliation info available
Shen K
No affiliation info available
Chen D
No affiliation info available
Liu X
No affiliation info available
Lin L
No affiliation info available
Feng X
No affiliation info available

MeSH

AminationCatalysisCrystallography, X-RayIndolesModels, MolecularMolecular StructureOrganometallic CompoundsOxindolesScandiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

20408167

Citation

Yang, Zhigang, et al. "Highly Enantioselective Synthesis of 3-amino-2-oxindole Derivatives: Catalytic Asymmetric Alpha-amination of 3-substituted 2-oxindoles With a Chiral Scandium Complex." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 16, no. 22, 2010, pp. 6632-7.
Yang Z, Wang Z, Bai S, et al. Highly enantioselective synthesis of 3-amino-2-oxindole derivatives: catalytic asymmetric alpha-amination of 3-substituted 2-oxindoles with a chiral scandium complex. Chemistry. 2010;16(22):6632-7.
Yang, Z., Wang, Z., Bai, S., Shen, K., Chen, D., Liu, X., Lin, L., & Feng, X. (2010). Highly enantioselective synthesis of 3-amino-2-oxindole derivatives: catalytic asymmetric alpha-amination of 3-substituted 2-oxindoles with a chiral scandium complex. Chemistry (Weinheim an Der Bergstrasse, Germany), 16(22), 6632-7. https://doi.org/10.1002/chem.201000126
Yang Z, et al. Highly Enantioselective Synthesis of 3-amino-2-oxindole Derivatives: Catalytic Asymmetric Alpha-amination of 3-substituted 2-oxindoles With a Chiral Scandium Complex. Chemistry. 2010 Jun 11;16(22):6632-7. PubMed PMID: 20408167.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly enantioselective synthesis of 3-amino-2-oxindole derivatives: catalytic asymmetric alpha-amination of 3-substituted 2-oxindoles with a chiral scandium complex. AU - Yang,Zhigang, AU - Wang,Zhen, AU - Bai,Sha, AU - Shen,Ke, AU - Chen,Donghui, AU - Liu,Xiaohua, AU - Lin,Lili, AU - Feng,Xiaoming, PY - 2010/4/22/entrez PY - 2010/4/22/pubmed PY - 2010/8/26/medline SP - 6632 EP - 7 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 16 IS - 22 N2 - A highly enantioselective alpha-amination of 3-substituted oxindoles with azodicarboxylates catalyzed by a chiral Sc(OTf)(3)/N,N'-dioxide complex (Tf: triflate) has been developed and affords the corresponding 3-amino-2-oxindole derivatives in high yields (up to 98%) with excellent enantioselectivities (up to 99% ee). The procedure is capable of tolerating a relatively wide range of substrates, and excellent results (92-96% ee) can also be obtained, even in the presence of 0.5 mol % of catalyst loading under mild conditions. These results showed the potential value of the catalytic approach. Moreover, with high synthetic versatility, the product could be easily transformed into optically active 3-amino-3-methyloxindole bearing a chiral quaternary stereogenic center. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/20408167/Highly_enantioselective_synthesis_of_3_amino_2_oxindole_derivatives:_catalytic_asymmetric_alpha_amination_of_3_substituted_2_oxindoles_with_a_chiral_scandium_complex_ DB - PRIME DP - Unbound Medicine ER -