TY - JOUR
T1 - Synthesis of Phostones via the Palladium-Catalyzed Ring Opening of Epoxy Vinyl Phosphonates
AU - Gnawali, Giri Raj
AU - Rath, Nigam P.
AU - Spilling, Christopher
N1 - The reaction of epoxy aldehydes with tetraethyl methylenediphosphonate gave γ,δ-epoxy vinyl phosphonates. The palladium-catalyzed addition of primary alcohols gave the monoprotected diols as single diastereoisomers. The trans- and cis-epoxides lead to opposite (syn and anti) diastereoisomers of the addition products.
PY - 2019/5/29
Y1 - 2019/5/29
N2 - The reaction of epoxy aldehydes with tetraethyl methylenediphosphonate gave γ,δ-epoxy vinyl phosphonates. The palladium-catalyzed addition of primary alcohols gave the monoprotected diols as single diastereoisomers. The trans - and cis -epoxides lead to opposite ( syn and anti ) diastereoisomers of the addition products. The alkene of the vinyl phosphonates was subjected to hydrogenation, and the resulting saturated phosphonates underwent base-catalyzed cyclization to give phostones with a very high diastereoselectivity in the formation of the new chiral center at the phosphorus atom.
AB - The reaction of epoxy aldehydes with tetraethyl methylenediphosphonate gave γ,δ-epoxy vinyl phosphonates. The palladium-catalyzed addition of primary alcohols gave the monoprotected diols as single diastereoisomers. The trans - and cis -epoxides lead to opposite ( syn and anti ) diastereoisomers of the addition products. The alkene of the vinyl phosphonates was subjected to hydrogenation, and the resulting saturated phosphonates underwent base-catalyzed cyclization to give phostones with a very high diastereoselectivity in the formation of the new chiral center at the phosphorus atom.
UR - https://pubs.acs.org/doi/10.1021/acs.joc.9b00905
UR - https://doi.org/10.1021/acs.joc.9b00905
U2 - 10.1021/acs.joc.9b00905
DO - 10.1021/acs.joc.9b00905
M3 - Article
VL - 84
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
ER -