N-heterocyclic carbene-catalyzed chemoselective cross-aza-benzoin reaction of enals with isatin-derived ketimines: Access to chiral quaternary aminooxindoles

Jianfeng Xu; Chengli Mou; Tingshun Zhu; Bao An Song; Yonggui Robin Chi

doi:10.1021/ol501286e

N-heterocyclic carbene-catalyzed chemoselective cross-aza-benzoin reaction of enals with isatin-derived ketimines: Access to chiral quaternary aminooxindoles

Jianfeng Xu, Chengli Mou, Tingshun Zhu, Bao An Song^*, Yonggui Robin Chi

^*Corresponding author for this work

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

96 Citations (Scopus)

Abstract

A chemo- and enantioselective cross-aza-benzoin reaction between enals and isatin-derived ketimines is disclosed. The high chemoselectivity (of the acyl anion reaction over enal α- and β-carbon reactions) is enabled by the electronic and steric properties of the N-heterocyclic carbene organocatalyst.

Original language	English
Pages (from-to)	3272-3275
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	12
DOIs	https://doi.org/10.1021/ol501286e
Publication status	Published - Jun 20 2014
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "A chemo- and enantioselective cross-aza-benzoin reaction between enals and isatin-derived ketimines is disclosed. The high chemoselectivity (of the acyl anion reaction over enal α- and β-carbon reactions) is enabled by the electronic and steric properties of the N-heterocyclic carbene organocatalyst.",

author = "Jianfeng Xu and Chengli Mou and Tingshun Zhu and Song, {Bao An} and Chi, {Yonggui Robin}",

year = "2014",

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journal = "Organic Letters",

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TY - JOUR

T1 - N-heterocyclic carbene-catalyzed chemoselective cross-aza-benzoin reaction of enals with isatin-derived ketimines

T2 - Access to chiral quaternary aminooxindoles

AU - Xu, Jianfeng

AU - Mou, Chengli

AU - Zhu, Tingshun

AU - Song, Bao An

AU - Chi, Yonggui Robin

PY - 2014/6/20

Y1 - 2014/6/20

N2 - A chemo- and enantioselective cross-aza-benzoin reaction between enals and isatin-derived ketimines is disclosed. The high chemoselectivity (of the acyl anion reaction over enal α- and β-carbon reactions) is enabled by the electronic and steric properties of the N-heterocyclic carbene organocatalyst.

AB - A chemo- and enantioselective cross-aza-benzoin reaction between enals and isatin-derived ketimines is disclosed. The high chemoselectivity (of the acyl anion reaction over enal α- and β-carbon reactions) is enabled by the electronic and steric properties of the N-heterocyclic carbene organocatalyst.

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U2 - 10.1021/ol501286e

DO - 10.1021/ol501286e

M3 - Article

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JO - Organic Letters

JF - Organic Letters

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ER -

N-heterocyclic carbene-catalyzed chemoselective cross-aza-benzoin reaction of enals with isatin-derived ketimines: Access to chiral quaternary aminooxindoles

Abstract

ASJC Scopus Subject Areas

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