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Synthesis of Phostones via the Palladium-Catalyzed Ring Opening of Epoxy Vinyl Phosphonates

Author:
Gnawali, Giri Raj, Rath, Nigam P., Spilling, Christopher D.
Source:
Journal of organic chemistry 2019 v.84 no.13 pp. 8724-8730
ISSN:
1520-6904
Subject:
aldehydes, catalytic activity, diastereomers, diastereoselectivity, epoxides, glycols, hydrogenation, organic chemistry, palladium, phosphonates, phosphorus
Abstract:
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.
Agid:
6496728