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

Jian Ping Chen; Wen Wen Chen; Yi Li; Ming Hua Xu

doi:10.1039/c5ob00063g

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

Jian Ping Chen, Wen Wen Chen, Yi Li, Ming Hua Xu

Research output: Contribution to journal › Article › peer-review

27 Scopus citations

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%).

Original language	English (US)
Pages (from-to)	3363-3370
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	13
Issue number	11
DOIs	https://doi.org/10.1039/c5ob00063g
State	Published - 2015
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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. / Chen, Jian Ping; Chen, Wen Wen; Li, Yi et al.
In: Organic and Biomolecular Chemistry, Vol. 13, No. 11, 2015, p. 3363-3370.

Research output: Contribution to journal › Article › peer-review

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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%).",

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AU - Chen, Jian Ping

AU - Chen, Wen Wen

AU - Li, Yi

AU - Xu, Ming Hua

N1 - Publisher Copyright: © The Royal Society of Chemistry 2015.

PY - 2015

Y1 - 2015

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%).

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%).

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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

Abstract

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