Nickel-Catalyzed Enantioselective Synthesis of Pre-Differentiated Homoallylic syn- or anti-1,2-Diols from Aldehydes and Dienol Ethers
Nickel catalysis allied with cyclodiphosphazane or VAPOL-derived phosphoramidite ligands provides selective access to monoprotected vicinal diols by reductive coupling of dienol ethers and aldehydes. The observed regioselectivity is unprecedented, in that the diene reacts at the least nucleophilic and most hindered C atom that is attached to the oxygen substituent rather than at the terminal position. Notably, both syn and anti diastereomers of the products can be accessed depending on the configuration of the diene partner with usually excellent diastereo- and enantioselectivity.
Davies, Thomas Q.,Murphy, John J.,Dousset, Maxime,Fürstner, Alois
supporting information
p. 13489 - 13494
(2021/09/11)
Stereocontrolled synthesis of α-trialkylsilyl-β,γ-unsaturated aldehydes via palladium (0) catalysis synthetic usefulness
The reaction of silicon substituted vinyloxiranes in the presence of catalytic amount of palladium (0) catalyst affords the title compounds. This new reaction proceeds smoothly, under very mild conditions and with complete chirality transfer. One-pot addition of selected organometallic nucleophiles to these aldehydes at very low temperature led to a highly selective preparation of the corresponding alcohols in very good yields. Influence of substituents on the silicon atom and of the ligands of palladium have been studied.
Le Bideau,Gilloir,Nilsson,Aubert,Malacria
p. 7487 - 7510
(2007/10/03)
Stereoselective Addition of Nucleophiles on α-Trialkylsilyl-β,γ-Unsaturated Aldehydes
Palladium(0)-catalyzed rearrangement of silicon substituted vinyloxiranes is depending on the size of the trialkylsilyl groups.Addition of organolithium or Grignard reagents on α-trialkylsilyl-β,γ-unsaturated aldehydes furnished the corresponding alcohols
Bideau, Franck Le,Gilloir, Fabienne,Nilsson, Ylva,Aubert, Corinne,Malacria, Max
p. 1641 - 1644
(2007/10/02)
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