Chiral Brønsted acid and gold catalyzed enantioselective synthesis of 1,8-dihydroindeno[2,1-b]pyrroles

Jianwen Jin, Yichao Zhao, Ella Min Ling Sze, Prasath Kothandaraman, Philip Wai Hong Chan

Research output: Contribution to journalArticleResearchpeer-review

Abstract

An enantioselective synthetic method for the preparation of 1,8-dihydroindeno[2,1-b]pyrroles that relies on the chiral Brønsted acid- and gold(I)-catalyzed dehydrative Nazarov-type electrocyclization (DNE)/hydroamination of electron-rich β-amino-1,4-enyols is described. Achieved in product yields up to 99% and enantiomeric excess (ee) values up to 99%, the asymmetric reaction provides access to a novel class of compounds containing both the privileged 1H-indene and pyrrole scaffold, which may lead to novel pharmacological applications. (Figure presented.).

Original languageEnglish
Pages (from-to)4744-4753
Number of pages10
JournalAdvanced Synthesis and Catalysis
Volume360
Issue number24
DOIs
Publication statusPublished - 21 Dec 2018

Keywords

  • asymmetric synthesis
  • chiral Brønsted acid catalysis
  • dehydrative Nazarov-type electrocyclization
  • gold catalysis
  • N-heterocyclic synthesis

Cite this

@article{8df9655295024e5c97fd1e06fa20f8a6,
title = "Chiral Br{\o}nsted acid and gold catalyzed enantioselective synthesis of 1,8-dihydroindeno[2,1-b]pyrroles",
abstract = "An enantioselective synthetic method for the preparation of 1,8-dihydroindeno[2,1-b]pyrroles that relies on the chiral Br{\o}nsted acid- and gold(I)-catalyzed dehydrative Nazarov-type electrocyclization (DNE)/hydroamination of electron-rich β-amino-1,4-enyols is described. Achieved in product yields up to 99{\%} and enantiomeric excess (ee) values up to 99{\%}, the asymmetric reaction provides access to a novel class of compounds containing both the privileged 1H-indene and pyrrole scaffold, which may lead to novel pharmacological applications. (Figure presented.).",
keywords = "asymmetric synthesis, chiral Br{\o}nsted acid catalysis, dehydrative Nazarov-type electrocyclization, gold catalysis, N-heterocyclic synthesis",
author = "Jianwen Jin and Yichao Zhao and Sze, {Ella Min Ling} and Prasath Kothandaraman and Chan, {Philip Wai Hong}",
year = "2018",
month = "12",
day = "21",
doi = "10.1002/adsc.201801178",
language = "English",
volume = "360",
pages = "4744--4753",
journal = "Advanced Synthesis and Catalysis",
issn = "1615-4150",
publisher = "Wiley-Blackwell",
number = "24",

}

Chiral Brønsted acid and gold catalyzed enantioselective synthesis of 1,8-dihydroindeno[2,1-b]pyrroles. / Jin, Jianwen; Zhao, Yichao; Sze, Ella Min Ling; Kothandaraman, Prasath; Chan, Philip Wai Hong.

In: Advanced Synthesis and Catalysis, Vol. 360, No. 24, 21.12.2018, p. 4744-4753.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Chiral Brønsted acid and gold catalyzed enantioselective synthesis of 1,8-dihydroindeno[2,1-b]pyrroles

AU - Jin, Jianwen

AU - Zhao, Yichao

AU - Sze, Ella Min Ling

AU - Kothandaraman, Prasath

AU - Chan, Philip Wai Hong

PY - 2018/12/21

Y1 - 2018/12/21

N2 - An enantioselective synthetic method for the preparation of 1,8-dihydroindeno[2,1-b]pyrroles that relies on the chiral Brønsted acid- and gold(I)-catalyzed dehydrative Nazarov-type electrocyclization (DNE)/hydroamination of electron-rich β-amino-1,4-enyols is described. Achieved in product yields up to 99% and enantiomeric excess (ee) values up to 99%, the asymmetric reaction provides access to a novel class of compounds containing both the privileged 1H-indene and pyrrole scaffold, which may lead to novel pharmacological applications. (Figure presented.).

AB - An enantioselective synthetic method for the preparation of 1,8-dihydroindeno[2,1-b]pyrroles that relies on the chiral Brønsted acid- and gold(I)-catalyzed dehydrative Nazarov-type electrocyclization (DNE)/hydroamination of electron-rich β-amino-1,4-enyols is described. Achieved in product yields up to 99% and enantiomeric excess (ee) values up to 99%, the asymmetric reaction provides access to a novel class of compounds containing both the privileged 1H-indene and pyrrole scaffold, which may lead to novel pharmacological applications. (Figure presented.).

KW - asymmetric synthesis

KW - chiral Brønsted acid catalysis

KW - dehydrative Nazarov-type electrocyclization

KW - gold catalysis

KW - N-heterocyclic synthesis

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VL - 360

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EP - 4753

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