Mukaiyama Aldol Reactions of Silyl Enolates Catalyzed by Iodine.

ChemInform ◽  
2004 ◽  
Vol 35 (32) ◽  
Author(s):  
Prodeep Phukan
2018 ◽  
Vol 14 ◽  
pp. 373-380 ◽  
Author(s):  
Anna-Lena Dreier ◽  
Andrej V Matsnev ◽  
Joseph S Thrasher ◽  
Günter Haufe

Aldol reactions belong to the most frequently used C–C bond forming transformations utilized particularly for the construction of complex structures. The selectivity of these reactions depends on the geometry of the intermediate enolates. Here, we have reacted octyl pentafluoro-λ6-sulfanylacetate with substituted benzaldehydes and acetaldehyde under the conditions of the silicon-mediated Mukaiyama aldol reaction. The transformations proceeded with high diastereoselectivity. In case of benzaldehydes with electron-withdrawing substituents in the para-position, syn-α-SF5-β-hydroxyalkanoic acid esters were produced. The reaction was also successful with meta-substituted benzaldehydes and o-fluorobenzaldehyde. In contrast, p-methyl-, p-methoxy-, and p-ethoxybenzaldehydes led selectively to aldol condensation products with (E)-configured double bonds in 30–40% yields. In preliminary experiments with an SF5-substituted acetic acid morpholide and p-nitrobenzaldehyde, a low amount of an aldol product was formed under similar conditions.


ChemInform ◽  
2011 ◽  
Vol 42 (14) ◽  
pp. no-no
Author(s):  
Claudio Curti ◽  
Lucia Battistini ◽  
Franca Zanardi ◽  
Gloria Rassu ◽  
Vincenzo Zambrano ◽  
...  

ChemInform ◽  
2014 ◽  
Vol 45 (19) ◽  
pp. no-no
Author(s):  
Taku Kitanosono ◽  
Thierry Ollevier ◽  
Shu Kobayashi

Sign in / Sign up

Export Citation Format

Share Document