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Sequential Suzuki/Asymmetric Aldol and Suzuki/Knoevenagel Reactions Under Aqueous Conditions
Author(s) -
Gruttadauria Michelangelo,
Bivona Lucia Anna,
Lo Meo Paolo,
Riela Serena,
Noto Renato
Publication year - 2012
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.201200092
Subject(s) - aldol reaction , chemistry , knoevenagel condensation , palladium , catalysis , organic chemistry , ionic liquid , suzuki reaction , organocatalysis , aqueous solution , combinatorial chemistry , enantioselective synthesis
Here we describe for the first time a sequential Suzuki/asymmetric aldol reaction. Such sequential approach was achieved through the combined use of an ionic liquid supported palladium catalyst and the organocatalyst trans ‐4‐(2,2‐diphenylacetoxy)proline. Suzuki and asymmetric aldol reactions were performed under aqueous conditions. The use of a palladium catalyst under basic conditions allowed also the first example of sequential Suzuki/Knoevenagel reaction. Reactions were carried out under aqueous conditions and products were isolated in good to high yields and, in the case of the Suzuki/aldol reaction, with diastereoselectivities up to 91:9 and enantioselectivities up to at least 99 %.