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Intramolecular Pd‐Catalyzed Formal anti ‐Carboalkoxylation of Alkynes: Access to Tetrasubstituted Enol Ethers
Author(s) -
Schitter Theresa,
Jones Peter G.,
Werz Daniel B.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201803721
Subject(s) - enol , intramolecular force , chemistry , organopalladium , catalysis , nucleophile , medicinal chemistry , triple bond , enol ether , palladium , organic chemistry , stereochemistry , double bond
An intramolecular Pd‐catalyzed formal anti ‐carboalkoxylation reaction is presented that provides access to tetrasubstituted enol ethers. The key to success is a cascade consisting of a formal anti ‐carbopalladation of a carbon–carbon triple bond followed by a nucleophilic attack of a hydroxy group at the emerging vinyl organopalladium species. The desired transformation proceeded smoothly with primary, secondary, and tertiary alcohols, and even with phenols. Depending on the substitution pattern of the enol ethers, a further Tsuji–Trost‐type step may occur resulting in oligocyclic ketals.