Abstract
Triethyl (1α,2α,3β)cyclopropane-1,2,3-tricarboxylate
(3aa ), as well as diethyl (4ab )
and dimethyl (1α,2β,3α)-1-acetylcyclopropane-2,3-dicarboxylate
(4bb ) have been prepared on a scale of
up to 60 g by Michael initiated ring-closure (MIRC) cyclopropanation
of dialkyl fumarates 1a ,b with
ethyl chloroacetate (2a ) and chloroacetone
(2b ) in 62%, 51% and
56% yield, respectively. For the success of the new procedure
it is essential to slowly add (within 5-7 h) the mixture
of compounds 1 and 2 to
a vigorously stirred suspension of K2 CO3 in
DMF in the presence of benzyltriethylammonium chloride.
Key words
cyclopropane - cyclizations - Michael additions - MIRC reaction - phase-transfer catalysis
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