Catalytic enantioselective inverse electron demand hetero-diels-alder reaction with allylsilanes

Yuki Matsumura; Takahiro Suzuki; Akira Sakakura; Kazuaki Ishihara

doi:10.1002/anie.201402934

Catalytic enantioselective inverse electron demand hetero-diels-alder reaction with allylsilanes

Yuki Matsumura, Takahiro Suzuki, Akira Sakakura, Kazuaki Ishihara

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

57 Citations (Scopus)

Abstract

The first diastereo- and enantioselective inverse electron demand hetero-Diels-Alder reaction of β,γ-unsaturated α-ketoesters with allylsilanes is described. Chiral copper(II) catalysts successfully activate the β,γ-unsaturated α-ketoesters and promote the reaction with allylsilanes with excellent enantioselectivities. This process represents a new entry to chiral oxanes.

Original language	English
Pages (from-to)	6131-6134
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	53
Issue number	24
DOIs	https://doi.org/10.1002/anie.201402934
Publication status	Published - Jun 10 2014

Keywords

Lewis acid
asymmetric catalysis
copper
cycloaddition
heterocycles

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201402934

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abstract = "The first diastereo- and enantioselective inverse electron demand hetero-Diels-Alder reaction of β,γ-unsaturated α-ketoesters with allylsilanes is described. Chiral copper(II) catalysts successfully activate the β,γ-unsaturated α-ketoesters and promote the reaction with allylsilanes with excellent enantioselectivities. This process represents a new entry to chiral oxanes.",

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author = "Yuki Matsumura and Takahiro Suzuki and Akira Sakakura and Kazuaki Ishihara",

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T1 - Catalytic enantioselective inverse electron demand hetero-diels-alder reaction with allylsilanes

AU - Matsumura, Yuki

AU - Suzuki, Takahiro

AU - Sakakura, Akira

AU - Ishihara, Kazuaki

PY - 2014/6/10

Y1 - 2014/6/10

N2 - The first diastereo- and enantioselective inverse electron demand hetero-Diels-Alder reaction of β,γ-unsaturated α-ketoesters with allylsilanes is described. Chiral copper(II) catalysts successfully activate the β,γ-unsaturated α-ketoesters and promote the reaction with allylsilanes with excellent enantioselectivities. This process represents a new entry to chiral oxanes.

AB - The first diastereo- and enantioselective inverse electron demand hetero-Diels-Alder reaction of β,γ-unsaturated α-ketoesters with allylsilanes is described. Chiral copper(II) catalysts successfully activate the β,γ-unsaturated α-ketoesters and promote the reaction with allylsilanes with excellent enantioselectivities. This process represents a new entry to chiral oxanes.

KW - Lewis acid

KW - asymmetric catalysis

KW - copper

KW - cycloaddition

KW - heterocycles

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 24

ER -

Catalytic enantioselective inverse electron demand hetero-diels-alder reaction with allylsilanes

Abstract

Keywords

ASJC Scopus subject areas

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