Intermolecular Gold(I)-Catalyzed Alkyne Carboalkoxylation Reactions for the Multicomponent Assembly of β-Alkoxy Ketones
作者:Danielle M. Schultz、Nicholas R. Babij、John P. Wolfe
DOI:10.1002/adsc.201200825
日期:2012.12.14
A new gold(I)-catalyzed multicomponent synthesis of β-alkoxy ketones from aldehydes, alcohols, and alkynes is described. This atom economical synthesis was achieved through the use of the gold complex (SPhos)AuNTf2 as a catalyst, and allows for the preparation of a diverse array of β-alkoxy ketone products. Mechanistic studies illustrate that these reactions proceed via gold(I)-catalyzed hydrolysis
In the presence of a catalytic amount of mesoporous aluminosilicate (Al-MCM-41), both allyltrimethylsilane and silyl enol ether reacted with various acetals under mild reaction conditions to afford the corresponding homoallyl ethers and beta-alkoxy ketones, respectively. The catalyst was easily recovered from the reaction mixture and could be reused in the same reaction without a significant loss of catalytic activity. Moreover, Al-MCM-41 exhibited high chemoselectivity for acetal over aldehyde in the reactions. (C) 2010 Elsevier Ltd. All rights reserved.