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The Use of Lewis Acids for Repairing Chemoselectivity of the Organocatalyzed Morita‐Baylis‐Hillman Reaction
Author(s) -
Fallek Amit,
Portnoy Moshe
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201900157
Subject(s) - chemoselectivity , lewis acids and bases , imidazole , catalysis , chemistry , situated , selectivity , organic chemistry , combinatorial chemistry , computer science , artificial intelligence
A substantial improvement in the chemoselectivity of the Morita‐Baylis‐Hillman reaction was realized by adding a diimino‐ or diaminopyridine coordination site within the backbone of bis‐imidazole organocatalysts and using Lewis acids situated at this coordination site. The optimal outcome of 90–95% selectivity was achieved by proper matching of the catalyst/additive pair, as well as their respective amount (0.4 equiv. of AgOAc per 1 equiv. of diaminopyridine‐incorporating catalyst).
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