Chiral anion catalysis in the enantioselective 1,4-reduction of the 1-benzopyrylium ion as a reactive intermediate

Masahiro Terada; Takuto Yamanaka; Yasunori Toda

doi:10.1002/chem.201302486

Chiral anion catalysis in the enantioselective 1,4-reduction of the 1-benzopyrylium ion as a reactive intermediate

Masahiro Terada, Takuto Yamanaka, Yasunori Toda

SCI - Chemistry

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

55 Citations (Scopus)

Abstract

Anionic! Novel chiral anion catalysis of the enantioselective 1,4-reduction of the 1-benzopyrylium ion by a chiral phosphoric acid was accomplished with a Hantzsch ester as the reducing agent. The enantioselective reduction established is composed of a two-step consecutive transformation involving stereoablative loss of the hydroxy group from racemic 2H-chromen-2-ol derivatives to generate the achiral 1-benzopyrylium ion as a reactive key intermediate.

Original language	English
Pages (from-to)	13658-13662
Number of pages	5
Journal	Chemistry - A European Journal
Volume	19
Issue number	41
DOIs	https://doi.org/10.1002/chem.201302486
Publication status	Published - 2013 Oct 4

Keywords

Brønsted acids
asymmetric catalysis
benzopyrylium
enantioselective reduction
organocatalysis

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201302486

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title = "Chiral anion catalysis in the enantioselective 1,4-reduction of the 1-benzopyrylium ion as a reactive intermediate",

abstract = "Anionic! Novel chiral anion catalysis of the enantioselective 1,4-reduction of the 1-benzopyrylium ion by a chiral phosphoric acid was accomplished with a Hantzsch ester as the reducing agent. The enantioselective reduction established is composed of a two-step consecutive transformation involving stereoablative loss of the hydroxy group from racemic 2H-chromen-2-ol derivatives to generate the achiral 1-benzopyrylium ion as a reactive key intermediate.",

keywords = "Br{\o}nsted acids, asymmetric catalysis, benzopyrylium, enantioselective reduction, organocatalysis",

author = "Masahiro Terada and Takuto Yamanaka and Yasunori Toda",

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doi = "10.1002/chem.201302486",

language = "English",

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T1 - Chiral anion catalysis in the enantioselective 1,4-reduction of the 1-benzopyrylium ion as a reactive intermediate

AU - Terada, Masahiro

AU - Yamanaka, Takuto

AU - Toda, Yasunori

PY - 2013/10/4

Y1 - 2013/10/4

N2 - Anionic! Novel chiral anion catalysis of the enantioselective 1,4-reduction of the 1-benzopyrylium ion by a chiral phosphoric acid was accomplished with a Hantzsch ester as the reducing agent. The enantioselective reduction established is composed of a two-step consecutive transformation involving stereoablative loss of the hydroxy group from racemic 2H-chromen-2-ol derivatives to generate the achiral 1-benzopyrylium ion as a reactive key intermediate.

AB - Anionic! Novel chiral anion catalysis of the enantioselective 1,4-reduction of the 1-benzopyrylium ion by a chiral phosphoric acid was accomplished with a Hantzsch ester as the reducing agent. The enantioselective reduction established is composed of a two-step consecutive transformation involving stereoablative loss of the hydroxy group from racemic 2H-chromen-2-ol derivatives to generate the achiral 1-benzopyrylium ion as a reactive key intermediate.

KW - Brønsted acids

KW - asymmetric catalysis

KW - benzopyrylium

KW - enantioselective reduction

KW - organocatalysis

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DO - 10.1002/chem.201302486

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SN - 0947-6539

VL - 19

SP - 13658

EP - 13662

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 41

ER -

Chiral anion catalysis in the enantioselective 1,4-reduction of the 1-benzopyrylium ion as a reactive intermediate

Abstract

Keywords

ASJC Scopus subject areas

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