Gold-Catalyzed 1,2-Acyloxy Migration/Coupling Cascade of Propargyl Diazoacetates: Synthesis of Isomycin Derivatives

Ming Bao; Xin Wang; Lihua Qiu; Wenhao Hu; Philip Wai Hong Chan; Xinfang Xu

doi:10.1021/acs.orglett.9b00392

Gold-Catalyzed 1,2-Acyloxy Migration/Coupling Cascade of Propargyl Diazoacetates: Synthesis of Isomycin Derivatives

Ming Bao
, Xin Wang
, Lihua Qiu
, Wenhao Hu
, Philip Wai Hong Chan^*
, Xinfang Xu

^*Corresponding author for this work

Sun Yat-Sen University
Soochow University
Monash University
University of Warwick

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

23 Scopus citations

Abstract

An efficient gold(I)-catalyzed carbocyclization reaction for the synthesis of isomycin derivatives from propargyl diazoacetates has been developed. The suggested cyclization pathway delineated the first example of a vinyl gold carbenoid species generated in situ from gold(I)-catalyzed 1,2-acyloxy migration and intercepted by a cross-coupling reaction with the remaining tethered diazo functionality. The use of protic additives was essential to regulating the reaction outcome by fine-tuning the catalytic preference of the gold(I) complex.

Original language	English
Pages (from-to)	1813-1817
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	6
DOIs	https://doi.org/10.1021/acs.orglett.9b00392
State	Published - 15 Mar 2019
Externally published	Yes

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10.1021/acs.orglett.9b00392

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title = "Gold-Catalyzed 1,2-Acyloxy Migration/Coupling Cascade of Propargyl Diazoacetates: Synthesis of Isomycin Derivatives",

abstract = "An efficient gold(I)-catalyzed carbocyclization reaction for the synthesis of isomycin derivatives from propargyl diazoacetates has been developed. The suggested cyclization pathway delineated the first example of a vinyl gold carbenoid species generated in situ from gold(I)-catalyzed 1,2-acyloxy migration and intercepted by a cross-coupling reaction with the remaining tethered diazo functionality. The use of protic additives was essential to regulating the reaction outcome by fine-tuning the catalytic preference of the gold(I) complex.",

author = "Ming Bao and Xin Wang and Lihua Qiu and Wenhao Hu and \{Hong Chan\}, \{Philip Wai\} and Xinfang Xu",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = mar,

day = "15",

doi = "10.1021/acs.orglett.9b00392",

language = "英语",

volume = "21",

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journal = "Organic Letters",

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T1 - Gold-Catalyzed 1,2-Acyloxy Migration/Coupling Cascade of Propargyl Diazoacetates

T2 - Synthesis of Isomycin Derivatives

AU - Bao, Ming

AU - Wang, Xin

AU - Qiu, Lihua

AU - Hu, Wenhao

AU - Hong Chan, Philip Wai

AU - Xu, Xinfang

PY - 2019/3/15

Y1 - 2019/3/15

N2 - An efficient gold(I)-catalyzed carbocyclization reaction for the synthesis of isomycin derivatives from propargyl diazoacetates has been developed. The suggested cyclization pathway delineated the first example of a vinyl gold carbenoid species generated in situ from gold(I)-catalyzed 1,2-acyloxy migration and intercepted by a cross-coupling reaction with the remaining tethered diazo functionality. The use of protic additives was essential to regulating the reaction outcome by fine-tuning the catalytic preference of the gold(I) complex.

AB - An efficient gold(I)-catalyzed carbocyclization reaction for the synthesis of isomycin derivatives from propargyl diazoacetates has been developed. The suggested cyclization pathway delineated the first example of a vinyl gold carbenoid species generated in situ from gold(I)-catalyzed 1,2-acyloxy migration and intercepted by a cross-coupling reaction with the remaining tethered diazo functionality. The use of protic additives was essential to regulating the reaction outcome by fine-tuning the catalytic preference of the gold(I) complex.

UR - https://www.scopus.com/pages/publications/85062834139

U2 - 10.1021/acs.orglett.9b00392

DO - 10.1021/acs.orglett.9b00392

M3 - 文章

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AN - SCOPUS:85062834139

SN - 1523-7060

VL - 21

SP - 1813

EP - 1817

JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

Gold-Catalyzed 1,2-Acyloxy Migration/Coupling Cascade of Propargyl Diazoacetates: Synthesis of Isomycin Derivatives

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