30567-26-1Relevant articles and documents
Efficient Access to All-Carbon Quaternary and Tertiary α-Functionalized Homoallyl-type Aldehydes from Ketones
Pace, Vittorio,Castoldi, Laura,Mazzeo, Eugenia,Rui, Marta,Langer, Thierry,Holzer, Wolfgang
supporting information, p. 12677 - 12682 (2017/09/08)
β,γ-Unsaturated aldehydes with all-carbon quaternary or tertiary α-centers were rapidly assembled from ketones through a unique synthetic operation consisting of 1) C1 homologation, 2) Lewis acid mediated epoxide–aldehyde isomerization, and 3) electrophilic trapping. The synthetic equivalence of a vinyl oxirane and a β,γ-unsaturated aldehyde is the key concept of this previously undisclosed tactic. Mechanistic studies and labeling experiments suggest that an aldehyde enolate is a crucial intermediate. The homologating carbenoid formation plays a critical role in determining the chemoselectivity.
Regioselective hydroformylation of allylic alcohols
Lightburn, Thomas E.,De Paolis, Omar A.,Cheng, Ka H.,Tan, Kian L.
, p. 2686 - 2689 (2011/06/28)
A highly regioselective hydroformylation of allylic alcohols is reported toward the synthesis of β-hydroxy-acid and aldehyde products. The selectivity is achieved through the use of a ligand that reversibly binds to alcohols in situ, allowing for a directed hydroformylation to occur. The application to trisubstituted olefins was also demonstrated, which yields a single diastereomer product consistent with a stereospecific addition of CO and hydrogen.
A new route to α,β-unsaturated aldehydes using the condensation of trimethylsilyl β-trimethylsilyl enol ethers with aldehydes
Duhamel, Lucette
, p. 7745 - 7748 (2007/10/02)
β-Trimethylsilyl enol ethers 1 (Z) obtained from β-bromoenolethers 2 were condensed with aliphatic and aromatic aldehydes in the presence of a catalytic quantity of trimethylsilyl triflate leading to ethylenic aldehydes 3 (E) with good yields (79-90%).
