Iridium-catalyzed enantioselective allylation of silyl enol ethers derived from ketones and α,β-unsaturated ketones

2015 ◽  
Vol 51 (98) ◽  
pp. 17471-17474 ◽  
Author(s):  
Xiao Liang ◽  
Kun Wei ◽  
Yu-Rong Yang
Keyword(s):  
Allylic Alcohols ◽  
Allylic Substitution ◽  
Substitution Reactions ◽  
Enol Ethers ◽  
Unsaturated Ketones ◽  
Silyl Enol Ethers

The unified Ir-catalyzed enantioselective allylic substitution reactions of silyl enol ethers derived from ketones and α,β-unsaturated ketones with branched, racemic allylic alcohols are described.

Molybdenum-Catalyzed Allylic Substitution in Glycals: A C-C Bond-Forming Ferrier-Type Reaction

2001 ◽  
Vol 66 (12) ◽  
pp. 1735-1745 ◽  
Author(s):  
Andrei V. Malkov ◽  
Benjamin P. Farn ◽  
Nigel Hussain ◽  
Pavel Kočovský
Keyword(s):  
Allylic Substitution ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Type Reaction ◽  
Bond Forming ◽  
Glycal Acetates ◽  
Glycosylation Reaction

The mild, Lewis-acidic complexes [Mo(CO)4Br2]2, (MeCN)2Mo(CO)3(SnCl3)Cl, and (acac)2Mo(OTf)2 have been found to catalyze the C(1)-specific C-glycosylation reaction of glycal acetates 1-3 with silyl enol ethers 4a-4c and electron-rich aromatics 5a, 5b (PhOMe, PhOH). While silyl enol ethers produce predominantly α-C-glycopyranosides (with 2 : 1 to 4 : 1 selectivity), aromatics tend to afford mainly β-C-glycopyranosides (2 : 1 to 3 : 1) in a thermodynamically controlled process.

W(CO)5(L)-Catalyzed Endo-Selective Cyclization of Allenyl Silyl Enol Ethers:  An Efficient Method for the Cyclopentene Annulation onto α,β-Unsaturated Ketones

2003 ◽  
Vol 5 (10) ◽  
pp. 1725-1728 ◽  
Author(s):  
Tomoya Miura ◽  
Koichi Kiyota ◽  
Hiroyuki Kusama ◽  
Kooyeon Lee ◽  
Hyunseok Kim ◽  
...  
Keyword(s):  
Efficient Method ◽  
Enol Ethers ◽  
Unsaturated Ketones ◽  
Silyl Enol Ethers
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