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A highly diastereoselective Friedel-Crafts reaction of indoles with isatin-derived N-sulfinyl ketimines towards the efficient synthesis of chiral tetrasubstituted 3-indolyl-3-aminooxindoles.
Org Biomol Chem. 2015 Mar 21; 13(11):3363-70.OB

Abstract

A Lewis acid promoted highly diastereoselective asymmetric Friedel-Crafts alkylation of indoles with isatin-derived N-tert-butanesulfinyl ketimines is described. The reaction can be accomplished with ease in the presence of a catalytic amount of Bi(OTf)3, providing a series of 3-indolyl-3-aminooxindoles in excellent diastereoselectivities (up to 98% de) and yields (up to 99%).

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Publisher Full Text (DOI)

Authors+Show Affiliations

Chen JP
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China. xumh@simm.ac.cn.
Chen WW
No affiliation info available
Li Y
No affiliation info available
Xu MH
No affiliation info available

MeSH

Crystallography, X-RayIminesIndolesIsatinModels, MolecularMolecular ConformationNitrilesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

25655031

Citation

Chen, Jian-Ping, et al. "A Highly Diastereoselective Friedel-Crafts Reaction of Indoles With Isatin-derived N-sulfinyl Ketimines Towards the Efficient Synthesis of Chiral Tetrasubstituted 3-indolyl-3-aminooxindoles." Organic & Biomolecular Chemistry, vol. 13, no. 11, 2015, pp. 3363-70.
Chen JP, Chen WW, Li Y, et al. A highly diastereoselective Friedel-Crafts reaction of indoles with isatin-derived N-sulfinyl ketimines towards the efficient synthesis of chiral tetrasubstituted 3-indolyl-3-aminooxindoles. Org Biomol Chem. 2015;13(11):3363-70.
Chen, J. P., Chen, W. W., Li, Y., & Xu, M. H. (2015). A highly diastereoselective Friedel-Crafts reaction of indoles with isatin-derived N-sulfinyl ketimines towards the efficient synthesis of chiral tetrasubstituted 3-indolyl-3-aminooxindoles. Organic & Biomolecular Chemistry, 13(11), 3363-70. https://doi.org/10.1039/c5ob00063g
Chen JP, et al. A Highly Diastereoselective Friedel-Crafts Reaction of Indoles With Isatin-derived N-sulfinyl Ketimines Towards the Efficient Synthesis of Chiral Tetrasubstituted 3-indolyl-3-aminooxindoles. Org Biomol Chem. 2015 Mar 21;13(11):3363-70. PubMed PMID: 25655031.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A highly diastereoselective Friedel-Crafts reaction of indoles with isatin-derived N-sulfinyl ketimines towards the efficient synthesis of chiral tetrasubstituted 3-indolyl-3-aminooxindoles. AU - Chen,Jian-Ping, AU - Chen,Wen-Wen, AU - Li,Yi, AU - Xu,Ming-Hua, PY - 2015/2/7/entrez PY - 2015/2/7/pubmed PY - 2015/9/30/medline SP - 3363 EP - 70 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 13 IS - 11 N2 - A Lewis acid promoted highly diastereoselective asymmetric Friedel-Crafts alkylation of indoles with isatin-derived N-tert-butanesulfinyl ketimines is described. The reaction can be accomplished with ease in the presence of a catalytic amount of Bi(OTf)3, providing a series of 3-indolyl-3-aminooxindoles in excellent diastereoselectivities (up to 98% de) and yields (up to 99%). SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/25655031/A_highly_diastereoselective_Friedel_Crafts_reaction_of_indoles_with_isatin_derived_N_sulfinyl_ketimines_towards_the_efficient_synthesis_of_chiral_tetrasubstituted_3_indolyl_3_aminooxindoles_ DB - PRIME DP - Unbound Medicine ER -

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