Citation: Liao Fumin, Du Yi, Zhou Feng, Zhou Jian. Au(I)/Chiral Tertiary Amine Catalyzed Tandem Olefination/Asymmetric Cyclization Reaction to Quaternary Spirocyclic Oxindoles[J]. Acta Chimica Sinica, ;2018, 76(11): 862-868. doi: 10.6023/A18060238 shu

Au(I)/Chiral Tertiary Amine Catalyzed Tandem Olefination/Asymmetric Cyclization Reaction to Quaternary Spirocyclic Oxindoles

Liao Fumin ^a,† ,
Du Yi ^b,† ,
Zhou Feng ^a ,
Zhou Jian ^a,c,d,,

a.
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University, Shanghai 200062
b.
Xinhua Hospital, Affiliated to Shanghai Jiaotong University School of Medicine, Shanghai 200032
c.
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062
d.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, Shanghai 200032

Corresponding author: Zhou Jian, jzhou@chem.ecnu.edu.cn

^†

Supporting information

http://sioc-journal.cn

Received Date: 18 June 2018
Available Online: 21 November 2018
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21472049)the National Natural Science Foundation of China 21472049

Figures(2)

We report an asymmetric tandem reaction realized by sequential Au(I)/chiral bifunctional tertiary amine catalysis. A tandem olefination/asymmetric cyclization reaction is developed, allowing facile synthesis of quaternary spirocyclic oxindoles in good yields and stereoselectivities from N-Ac protected diazooxindoles 1, monofluorinated enol silyl ethers 2 and 2-tosylaminochalcone 4. The initial cross coupling reaction of diazooxindole and fluorinated enol silyl ethers, catalyzed by 3.0 mol% IPrAuBF₄, readily afforded 3-alkenyloxindoles for the subsequent Michael/Michael addition of 2-tosylaminochalcone catalyzed by 5.0~10.0 mol% chiral bifunctional tertiary amine-squaramide C1. The tandem reaction was performed by the following general procedure. Under an atmosphere of N₂, to an oven-dried Schlenk tube were added IPrAuCl (6.0 mg, 0.0099 mmol, 3.3 mol%) and AgBF₄ (1.8 mg, 0.0090 mmol, 3.0 mol%), followed by anhydrous CH₂Cl₂ (1.0 mL). The resulting mixture was stirred at 25℃ for 0.5 h and then cooled down to 0℃. After ethers 2 (1.5 equiv.) was added in one-portion, a solution of diazooxindoles 1 in 1.5 mL of CH₂Cl₂ was added slowly by a syringe pump in 20 minutes. The reaction was stirred at 0℃ till full consumption of 1 by TLC analysis. After the successive addition of C1 and 4 (1.1 equiv.), the reaction was warmed to 25℃ and stirred till full consumption of 3, and the mixture was directly subjected to the column chromatography by using petroleum ether/dichloromethane (1/2.5, V/V) as the eluent to give the desired spirocyclic oxindoles 5. The diastereoselectivities of 5 (>20:1) were determined by ¹H NMR analysis of the crude reaction mixture. The key step of this tandem sequence is the cross coupling reaction of monofluorinated enol silyl ethers and donor-acceptor diazo reagents. We further examined the substrates scope of acyclic aryl diazoacetates and fluorinated enol silyl ethers by using 1.0 mol% IPrAuSbF₆ as catalyst, providing a new method for the efficient synthesis of trisubstituted alkenes.
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