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

Jianping Chen, Wen Wen Chen, Yi Li, Ming Hua Xu

Research output: Contribution to journalArticle

16 Citations (Scopus)

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%). This journal is

Original languageEnglish (US)
Pages (from-to)3363-3370
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume13
Issue number11
DOIs
StatePublished - Jan 1 2015
Externally publishedYes

Fingerprint

Friedel-Craft reaction
Friedel-Crafts reaction
Isatin
Indoles
Lewis Acids
alkylation
indoles
Alkylation
vehicles
acids
synthesis
Bi(OTf)3
ketimine

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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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{\%}). This journal is",
author = "Jianping Chen and Chen, {Wen Wen} and Yi Li and Xu, {Ming Hua}",
year = "2015",
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language = "English (US)",
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publisher = "Royal Society of Chemistry",
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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, Jianping

AU - Chen, Wen Wen

AU - Li, Yi

AU - Xu, Ming Hua

PY - 2015/1/1

Y1 - 2015/1/1

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%). This journal is

AB - 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%). This journal is

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U2 - 10.1039/c5ob00063g

DO - 10.1039/c5ob00063g

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