Copper Hydride Catalyzed Reductive Claisen Rearrangements

Kong Ching Wong; Elvis Ng; Wing Tak Wong; Pauline Chiu

doi:10.1002/chem.201504870

Copper Hydride Catalyzed Reductive Claisen Rearrangements

Kong Ching Wong, Elvis Ng, Wing Tak Wong, Pauline Chiu

Research output: Journal article publication › Journal article › Academic research › peer-review

19 Citations (Scopus)

Abstract

KGaA, Weinheim. An efficient reductive Claisen rearrangement, catalyzed by in situ generated copper hydride and stoichiometric in diethoxymethylsilane, has been developed. Yields of up to 95 ;% with good to excellent diastereoselectivities were observed in this reaction. Mechanistic studies showed that the stereospecific rearrangement proceeded via a chair transition state of (E)-silyl ketene acetals as intermediates and not via the copper enolates.

Original language	English
Pages (from-to)	3709-3712
Number of pages	4
Journal	Chemistry - A European Journal
Volume	22
Issue number	11
DOIs	https://doi.org/10.1002/chem.201504870
Publication status	Published - 7 Mar 2016

Keywords

Claisen rearrangements
copper
hydride
reduction
silanes

ASJC Scopus subject areas

General Chemistry

More information

10.1002/chem.201504870

http://hdl.handle.net/10397/101612

Cite this

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abstract = "KGaA, Weinheim. An efficient reductive Claisen rearrangement, catalyzed by in situ generated copper hydride and stoichiometric in diethoxymethylsilane, has been developed. Yields of up to 95 ;% with good to excellent diastereoselectivities were observed in this reaction. Mechanistic studies showed that the stereospecific rearrangement proceeded via a chair transition state of (E)-silyl ketene acetals as intermediates and not via the copper enolates.",

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AU - Wong, Kong Ching

AU - Ng, Elvis

AU - Wong, Wing Tak

AU - Chiu, Pauline

PY - 2016/3/7

Y1 - 2016/3/7

N2 - KGaA, Weinheim. An efficient reductive Claisen rearrangement, catalyzed by in situ generated copper hydride and stoichiometric in diethoxymethylsilane, has been developed. Yields of up to 95 ;% with good to excellent diastereoselectivities were observed in this reaction. Mechanistic studies showed that the stereospecific rearrangement proceeded via a chair transition state of (E)-silyl ketene acetals as intermediates and not via the copper enolates.

AB - KGaA, Weinheim. An efficient reductive Claisen rearrangement, catalyzed by in situ generated copper hydride and stoichiometric in diethoxymethylsilane, has been developed. Yields of up to 95 ;% with good to excellent diastereoselectivities were observed in this reaction. Mechanistic studies showed that the stereospecific rearrangement proceeded via a chair transition state of (E)-silyl ketene acetals as intermediates and not via the copper enolates.

KW - Claisen rearrangements

KW - copper

KW - hydride

KW - reduction

KW - silanes

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DO - 10.1002/chem.201504870

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JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 11

ER -

Copper Hydride Catalyzed Reductive Claisen Rearrangements

Abstract

Keywords

ASJC Scopus subject areas

More information

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