Synthesis of Phostones via the Palladium-Catalyzed Ring Opening of Epoxy Vinyl Phosphonates.
J Org Chem
; 84(13): 8724-8730, 2019 07 05.
Article
in En
| MEDLINE
| ID: mdl-31140269
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.
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Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
J Org Chem
Year:
2019
Document type:
Article
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