Catalytic asymmetric tandem Friedel-Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans

Jiahuan Peng; Da Ming Du

doi:10.3762/bjoc.9.137

Catalytic asymmetric tandem Friedel-Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans

Jiahuan Peng, Da Ming Du^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

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

11 Citations (Scopus)

Abstract

The enantioselective tandem Friedel-Crafts alkylation/Michael addition reaction of indoles with nitroolefin enoates catalyzed by a diphenylamine-linked bis(oxazoline)-Zn(OTf)2 complex was investigated. This tandem reaction afforded functionalized chiral chromans in good yields with moderate to high stereoselectivities (up to 95:5 dr, up to 99% ee).

Original language	English
Pages (from-to)	1210-1216
Number of pages	7
Journal	Beilstein Journal of Organic Chemistry
Volume	9
DOIs	https://doi.org/10.3762/bjoc.9.137
Publication status	Published - 24 Jun 2013

Keywords

Asymmetric catalysis
Bis(oxazoline)
Chroman
Friedel-Crafts alkylation
Tandem reaction

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abstract = "The enantioselective tandem Friedel-Crafts alkylation/Michael addition reaction of indoles with nitroolefin enoates catalyzed by a diphenylamine-linked bis(oxazoline)-Zn(OTf)2 complex was investigated. This tandem reaction afforded functionalized chiral chromans in good yields with moderate to high stereoselectivities (up to 95:5 dr, up to 99\% ee).",

keywords = "Asymmetric catalysis, Bis(oxazoline), Chroman, Friedel-Crafts alkylation, Tandem reaction",

author = "Jiahuan Peng and Du, \{Da Ming\}",

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doi = "10.3762/bjoc.9.137",

language = "English",

volume = "9",

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AU - Peng, Jiahuan

AU - Du, Da Ming

PY - 2013/6/24

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N2 - The enantioselective tandem Friedel-Crafts alkylation/Michael addition reaction of indoles with nitroolefin enoates catalyzed by a diphenylamine-linked bis(oxazoline)-Zn(OTf)2 complex was investigated. This tandem reaction afforded functionalized chiral chromans in good yields with moderate to high stereoselectivities (up to 95:5 dr, up to 99% ee).

AB - The enantioselective tandem Friedel-Crafts alkylation/Michael addition reaction of indoles with nitroolefin enoates catalyzed by a diphenylamine-linked bis(oxazoline)-Zn(OTf)2 complex was investigated. This tandem reaction afforded functionalized chiral chromans in good yields with moderate to high stereoselectivities (up to 95:5 dr, up to 99% ee).

KW - Asymmetric catalysis

KW - Bis(oxazoline)

KW - Chroman

KW - Friedel-Crafts alkylation

KW - Tandem reaction

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U2 - 10.3762/bjoc.9.137

DO - 10.3762/bjoc.9.137

M3 - Article

AN - SCOPUS:84879986317

SN - 1860-5397

VL - 9

SP - 1210

EP - 1216

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

Catalytic asymmetric tandem Friedel-Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans

Abstract

Keywords

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