Gold‐Catalyzed [4+2]‐ and [3+3]‐Annulations of Ynamides with 1‐Yn‐3‐ols to Access Six‐Membered Carbocycles and Oxacycles via Three Distinct Cyclizations
作者： Sovan Sundar Giri , Rai-Shung Liu
关键词: Organic chemistry 、 Enol 、 Yield (chemistry) 、 Catalysis 、 Claisen rearrangement 、 Chemistry 、 Reaction sequence
摘要: Abstract. Three distinct strategies for catalytic annulations between ynamides and 1-yn-3-ols are described; resulting carbo- heterocycles were produced efficiently in one-pot operations using a gold catalyst. The chemoselectivities of these controlled by variations the substituents 1-yn-3-ols. This reaction sequence involves initial alkoxylations ynamides, followed Claisen rearrangement propargylic enol ethers, ended with 6-endo-trig cyclizations 1-allenyl-5-amide intermediates. Among cascade annulations, 5-allenyl-1-amides to yield 5,6-dihydro-2-pyranones 6-alkylenecyclohex-2-ene-1-carboxamides unprecedented literature.
sci-hub.se 参考文章(68)
Frédérique Tellier, Max Audouin, Raymond Sauvêtre, Synthesis of α-trifluoromethyl unsaturated acids and derivatives Journal of Fluorine Chemistry. ,vol. 113, pp. 167- 175 ,(2002) , 10.1016/S0022-1139(01)00542-5
Norbert Krause, Christian Winter, Gold-catalyzed nucleophilic cyclization of functionalized allenes: a powerful access to carbo- and heterocycles. Chemical Reviews. ,vol. 111, pp. 1994- 2009 ,(2011) , 10.1021/CR1004088
Cole A. Witham, Pablo Mauleón, Nathan D. Shapiro, Benjamin D. Sherry, F. Dean Toste, Gold(I)-catalyzed oxidative rearrangements. Journal of the American Chemical Society. ,vol. 129, pp. 5838- 5839 ,(2007) , 10.1021/JA071231+
Xiao-Na Wang, Hyun-Suk Yeom, Li-Chao Fang, Shuzhong He, Zhi-Xiong Ma, Brant L. Kedrowski, Richard P. Hsung, Ynamides in Ring Forming Transformations Accounts of Chemical Research. ,vol. 47, pp. 560- 578 ,(2014) , 10.1021/AR400193G
Steven M. Bachrach, The gem-Dimethyl Effect Revisited Journal of Organic Chemistry. ,vol. 73, pp. 2466- 2468 ,(2008) , 10.1021/JO702665R
Eloísa Jiménez-Núñez, Antonio M. Echavarren, Gold-catalyzed cycloisomerizations of enynes: a mechanistic perspective. Chemical Reviews. ,vol. 108, pp. 3326- 3350 ,(2008) , 10.1021/CR0684319
G. Saucy, R. Marbet, Über eine neuartige Synthese von β‐Ketoallenen durch Reaktion von tertiären Acetylencarbinolen mit Vinyläthern eine ergiebige methode zur darstellung des Pseudojonons und verwandter verbindungen Helvetica Chimica Acta. ,vol. 50, pp. 1158- 1167 ,(1967) , 10.1002/HLCA.19670500423
Tien-Yau Luh, Ziqiang Hu, Thorpe–Ingold effect in organosilicon chemistry Dalton Transactions. ,vol. 39, pp. 9185- 9192 ,(2010) , 10.1039/C0DT00105H
Chung-Meng Chao, Denis Beltrami, Patrick Y. Toullec, Véronique Michelet, Asymmetric Au(I)-catalyzed synthesis of bicyclo[4.1.0]heptene derivatives via a cycloisomerization process of 1,6-enynes Chemical Communications. pp. 6988- 6990 ,(2009) , 10.1039/B913554E
Birgit Gockel, Norbert Krause, Golden times for allenes: Gold-catalyzed cycloisomerization of beta-hydroxyallenes to dihydropyrans. Organic Letters. ,vol. 8, pp. 4485- 4488 ,(2006) , 10.1021/OL061669Z