Auxiliary-controlled Site Selectivity [4+2] Cycloaddition Reactions of a,b-Unsaturated Carbonyl Compounds to 4,4-Bis(trifluoromethyl)-substituted Hetero-1,3-Dienes

Heterocycles ◽  
1994 ◽  
Vol 37 (3) ◽  
pp. 1719 ◽  
Author(s):  
Klaus Burger ◽  
J嗷g Cyrener
Keyword(s):  
Carbonyl Compounds ◽  
Cycloaddition Reactions ◽  
Site Selectivity

Tandem dihetero-Diels–Alder and Huisgen cycloaddition reactions. Synthesis, crystal structure and hydrolysis of the novel cage phosphoranes

2018 ◽  
Vol 5 (21) ◽  
pp. 3113-3128 ◽  
Author(s):  
Nadezhda R. Khasiyatullina ◽  
Tamara A. Baronova ◽  
Ekaterina V. Mironova ◽  
Robert R. Fayzullin ◽  
Igor A. Litvinov ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Carbonyl Compounds ◽  
Diels Alder ◽  
Cycloaddition Reactions ◽  
The Novel ◽  
Hydrolysis Of

The reaction of 2-(1-phenylvinyloxy)benzo-1,3,2-dioxaphosphole with activated carbonyl compounds leads to the stereoselective formation of cage phosphoranes.

Novel Addition and [3+2] Cycloaddition Reactions of Stannyl- and Silyl-ortho-carboranes to Carbonyl Compounds

1999 ◽  
Vol 64 (5) ◽  
pp. 829-846 ◽  
Author(s):  
Hiroyuki Nakamura ◽  
Yoshinori Yamamoto
Keyword(s):  
Carbonyl Compounds ◽  
Addition Reaction ◽  
Cycloaddition Reactions ◽  
Tetrabutylammonium Fluoride ◽  
High Yields

Stannyl- and silyl-ortho-carboranes serve as an ortho-carborane carbanion equivalents in the addition reaction to aldehydes. The reaction of (tributylstannyl)-ortho-carborane 2 with aldehydes 4 in the presence of palladium(0) catalysts gave the corresponding (ortho-carboranyl) carbinols 5 in good to high yields. The reaction of (trimethylsilyl)-ortho-carborane 3 with aldehydes 4 in the presence of tetrabutylammonium fluoride (TBAF) gave the corresponding (ortho-carboranyl) carbinols 5 in high yields. Furthermore, (trimethylsilyl)-ortho-carborane 3 underwent a facile [3+2] annulation reaction with various α,β-unsaturated enals and enones in the presence of tetrabutylammonium fluoride, giving the corresponding five-membered carboracyclic products 14 in good to high yields.

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