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Highly Selective Syn Addition of 1,3‐Diones to Internal Ynamides Catalyzed by Zinc Iodide
Author(s) -
Plamont Rémi,
Graux Lionel V.,
Clavier Hervé
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701690
Subject(s) - chemistry , catalysis , adduct , zinc , iodide , nucleophile , lewis acids and bases , combinatorial chemistry , organic chemistry
1,3‐Diones are already established as nucleophiles to perform additions to ynamides; the highly selective hydroalkoxylation of internal ynamides is now described. Several catalytic systems have been compared to perform this transformation, including transition‐metal‐based catalysts and Lewis acids. ZnI 2 was found to be both very active and highly selective providing only E adducts through a syn addition. Investigation of the scope and limitations showed that this catalyst was compatible with various functional groups. In addition to seventeen examples of ynamide hydroalkoxylation, one example of ynamide hydroarylation is reported.