Gold-Catalyzed Oxidative Cyclization/Aldol Addition of Homopropargyl Alcohols with Isatins

Ju Cai; Xin Wang; Yu Qian; Lihua Qiu; Wenhao Hu; Xinfang Xu

doi:10.1021/acs.orglett.8b03502

Gold-Catalyzed Oxidative Cyclization/Aldol Addition of Homopropargyl Alcohols with Isatins

Ju Cai, Xin Wang, Yu Qian, Lihua Qiu, Wenhao Hu, Xinfang Xu

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

37 Scopus citations

Abstract

A novel gold-catalyzed oxidative cyclization/aldol addition of homopropargyl alcohols with isatins has been developed that provides an effective access to the 3-hydroxyoxindoles in high yields under mild reaction conditions with high diastereoselectivities. In comparison with disclosed transformations of alkyne oxidations via an α-oxo gold carbene route, this is the first example of an aldol-type interception of an ylide (or its enolate form) intermediate with alkyne as a safe and readily available nondiazo carbene precursor.

Original language	English
Pages (from-to)	369-372
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	2
DOIs	https://doi.org/10.1021/acs.orglett.8b03502
State	Published - 18 Jan 2019
Externally published	Yes

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title = "Gold-Catalyzed Oxidative Cyclization/Aldol Addition of Homopropargyl Alcohols with Isatins",

abstract = "A novel gold-catalyzed oxidative cyclization/aldol addition of homopropargyl alcohols with isatins has been developed that provides an effective access to the 3-hydroxyoxindoles in high yields under mild reaction conditions with high diastereoselectivities. In comparison with disclosed transformations of alkyne oxidations via an α-oxo gold carbene route, this is the first example of an aldol-type interception of an ylide (or its enolate form) intermediate with alkyne as a safe and readily available nondiazo carbene precursor.",

author = "Ju Cai and Xin Wang and Yu Qian and Lihua Qiu and Wenhao Hu and Xinfang Xu",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2019",

month = jan,

day = "18",

doi = "10.1021/acs.orglett.8b03502",

language = "英语",

volume = "21",

pages = "369--372",

journal = "Organic Letters",

issn = "1523-7060",

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TY - JOUR

T1 - Gold-Catalyzed Oxidative Cyclization/Aldol Addition of Homopropargyl Alcohols with Isatins

AU - Cai, Ju

AU - Wang, Xin

AU - Qian, Yu

AU - Qiu, Lihua

AU - Hu, Wenhao

AU - Xu, Xinfang

PY - 2019/1/18

Y1 - 2019/1/18

N2 - A novel gold-catalyzed oxidative cyclization/aldol addition of homopropargyl alcohols with isatins has been developed that provides an effective access to the 3-hydroxyoxindoles in high yields under mild reaction conditions with high diastereoselectivities. In comparison with disclosed transformations of alkyne oxidations via an α-oxo gold carbene route, this is the first example of an aldol-type interception of an ylide (or its enolate form) intermediate with alkyne as a safe and readily available nondiazo carbene precursor.

AB - A novel gold-catalyzed oxidative cyclization/aldol addition of homopropargyl alcohols with isatins has been developed that provides an effective access to the 3-hydroxyoxindoles in high yields under mild reaction conditions with high diastereoselectivities. In comparison with disclosed transformations of alkyne oxidations via an α-oxo gold carbene route, this is the first example of an aldol-type interception of an ylide (or its enolate form) intermediate with alkyne as a safe and readily available nondiazo carbene precursor.

UR - https://www.scopus.com/pages/publications/85059643727

U2 - 10.1021/acs.orglett.8b03502

DO - 10.1021/acs.orglett.8b03502

M3 - 文章

C2 - 30596509

AN - SCOPUS:85059643727

SN - 1523-7060

VL - 21

SP - 369

EP - 372

JO - Organic Letters

JF - Organic Letters

IS - 2

ER -

Gold-Catalyzed Oxidative Cyclization/Aldol Addition of Homopropargyl Alcohols with Isatins

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