Gold(I)-Catalyzed Desymmetrization of 1,4-Dienes by an Enantioselective Tandem Alkoxylation/Claisen Rearrangement

Hongmiao Wu; Weiwei Zi; Guigen Li; Hongjian Lu; F. Dean Toste

doi:10.1002/anie.201503357

Gold(I)-Catalyzed Desymmetrization of 1,4-Dienes by an Enantioselective Tandem Alkoxylation/Claisen Rearrangement

Hongmiao Wu, Weiwei Zi, Guigen Li, Hongjian Lu, F. Dean Toste

Chemistry and Biochemistry

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

47 Scopus citations

Abstract

An enantioselective alkoxylation/Claisen rearrangement reaction was achieved by a strategic desymmetrization of 1,4-dienes under the catalysis of (S)-DTBM-Segphos(AuCl)₂/AgBF₄. This reaction system was highly selective for the formation of 3,3-rearrangement products, providing cycloheptenes with various substitutions in good yield and good to excellent enantioselectivity. This transformation was further extended to bicyclic ring substrates, providing the opportunity to easily assemble 5,6- and 6,7-fused ring systems.

Original language	English
Pages (from-to)	8529-8532
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	29
DOIs	https://doi.org/10.1002/anie.201503357
State	Published - Jul 13 2015

Keywords

Claisen rearrangement
alkoxylation
desymmetrization
enantioselectivity
gold

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10.1002/anie.201503357

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title = "Gold(I)-Catalyzed Desymmetrization of 1,4-Dienes by an Enantioselective Tandem Alkoxylation/Claisen Rearrangement",

abstract = "An enantioselective alkoxylation/Claisen rearrangement reaction was achieved by a strategic desymmetrization of 1,4-dienes under the catalysis of (S)-DTBM-Segphos(AuCl)2/AgBF4. This reaction system was highly selective for the formation of 3,3-rearrangement products, providing cycloheptenes with various substitutions in good yield and good to excellent enantioselectivity. This transformation was further extended to bicyclic ring substrates, providing the opportunity to easily assemble 5,6- and 6,7-fused ring systems.",

keywords = "Claisen rearrangement, alkoxylation, desymmetrization, enantioselectivity, gold",

author = "Hongmiao Wu and Weiwei Zi and Guigen Li and Hongjian Lu and Toste, {F. Dean}",

note = "Publisher Copyright: {\textcopyright} 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

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doi = "10.1002/anie.201503357",

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T1 - Gold(I)-Catalyzed Desymmetrization of 1,4-Dienes by an Enantioselective Tandem Alkoxylation/Claisen Rearrangement

AU - Wu, Hongmiao

AU - Zi, Weiwei

AU - Li, Guigen

AU - Lu, Hongjian

AU - Toste, F. Dean

PY - 2015/7/13

Y1 - 2015/7/13

N2 - An enantioselective alkoxylation/Claisen rearrangement reaction was achieved by a strategic desymmetrization of 1,4-dienes under the catalysis of (S)-DTBM-Segphos(AuCl)2/AgBF4. This reaction system was highly selective for the formation of 3,3-rearrangement products, providing cycloheptenes with various substitutions in good yield and good to excellent enantioselectivity. This transformation was further extended to bicyclic ring substrates, providing the opportunity to easily assemble 5,6- and 6,7-fused ring systems.

AB - An enantioselective alkoxylation/Claisen rearrangement reaction was achieved by a strategic desymmetrization of 1,4-dienes under the catalysis of (S)-DTBM-Segphos(AuCl)2/AgBF4. This reaction system was highly selective for the formation of 3,3-rearrangement products, providing cycloheptenes with various substitutions in good yield and good to excellent enantioselectivity. This transformation was further extended to bicyclic ring substrates, providing the opportunity to easily assemble 5,6- and 6,7-fused ring systems.

KW - Claisen rearrangement

KW - alkoxylation

KW - desymmetrization

KW - enantioselectivity

KW - gold

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AN - SCOPUS:84946715627

SN - 1433-7851

VL - 54

SP - 8529

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 29

ER -

Gold(I)-Catalyzed Desymmetrization of 1,4-Dienes by an Enantioselective Tandem Alkoxylation/Claisen Rearrangement

Abstract

Keywords

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