1 3
Topics in Current Chemistry (2018) 376:46
(EDA). Aliquots regularly taken at the outlet of the reactor were analyzed in order
to check the progress of the reaction and the composition in cyclopropanes 72 and
73, by-products fumarates 74 and maleates 75. High flow rates led to a decrease
in cyclopropanes yield, while better conversions were observed at lower flow rates.
The moderate yield of cyclopropanes could be explained by the EDA dimerization
to produce ethyl fumarate and maleate, reducing the chemoselectivity of the process,
besides, both regio and enantioselectivites were good.
Hashimoto developed the first example of a continuous flow system with a heterogeneous polymer-supported dirhodium(II) complex 76 (Scheme 33). The catalyst 76 derived from 2-(trifluoromethyl)styrene, as a comonomer, was successfully
applied in tandem carbonyl ylide formation-cycloaddition reactions of 2-diazo3,6-diketoesters 77 with phenylacetylene as dipolarophile in CF 3 C 6 H 5 , observing
Scheme 32 Continuous-flow cyclopropanation reaction between styrene and EDA, catalyzed by RuPybox miniflow reactor
Scheme 33 Enantioselective intermolecular cycloaddition of 2-diazo-3,6-diketoester with phenylacetylene under continuous flow conditions
57
Reprinted from the journal
Topics in Current Chemistry (2018) 376:46
(EDA). Aliquots regularly taken at the outlet of the reactor were analyzed in order
to check the progress of the reaction and the composition in cyclopropanes 72 and
73, by-products fumarates 74 and maleates 75. High flow rates led to a decrease
in cyclopropanes yield, while better conversions were observed at lower flow rates.
The moderate yield of cyclopropanes could be explained by the EDA dimerization
to produce ethyl fumarate and maleate, reducing the chemoselectivity of the process,
besides, both regio and enantioselectivites were good.
Hashimoto developed the first example of a continuous flow system with a heterogeneous polymer-supported dirhodium(II) complex 76 (Scheme 33). The catalyst 76 derived from 2-(trifluoromethyl)styrene, as a comonomer, was successfully
applied in tandem carbonyl ylide formation-cycloaddition reactions of 2-diazo3,6-diketoesters 77 with phenylacetylene as dipolarophile in CF 3 C 6 H 5 , observing
Scheme 32 Continuous-flow cyclopropanation reaction between styrene and EDA, catalyzed by RuPybox miniflow reactor
Scheme 33 Enantioselective intermolecular cycloaddition of 2-diazo-3,6-diketoester with phenylacetylene under continuous flow conditions
57
Reprinted from the journal