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

Author:
Cai, Ju, Wang, Xin, Qian, Yu, Qiu, Lihua, Hu, Wenhao, Xu, Xinfang
Source:
Organic letters 2018 v.21 no.2 pp. 369-372
ISSN:
1523-7052
Subject:
alcohols, alkynes, carbenes, chemical reactions, chemical structure, diastereoselectivity, gold
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.
Agid:
6272217