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Practical Synthesis of ( E )‐α,β‐Unsaturated Carboxylic Acids Using a One‐Pot Hydroformylation/Decarboxylative Knoevenagel Reaction Sequence
Author(s) -
Kemme Susanne T.,
Šmejkal Tomáš,
Breit Bernhard
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700595
Subject(s) - chemistry , hydroformylation , knoevenagel condensation , regioselectivity , aldehyde , organic chemistry , reaction conditions , carboxylic acid , functional group , catalysis , rhodium , polymer
Combining the regioselective room temperature/ambient pressure hydroformylation and a modification of the Doebner–Knoevenagel reaction allowed for the development of an efficient, one‐pot procedure for the synthesis of ( E )‐α,β‐unsaturated carboxylic acids. The reaction proceeds under mild conditions, tolerates a variety of functional groups and gives ( E )‐α,β‐unsaturated carboxylic acids in good yields and with excellent regio‐ and stereocontrol. The practicability of this process has been demonstrated by a short protecting group‐free synthesis of the queen honeybee pheromones 9‐ODA [( E )‐9‐oxodec‐2‐enoic acid] and 9‐HDA [( E )‐9‐hydroxydec‐2‐enoic acid].