Preparation of functionalized Z-olefins using 1,1-dimetalloalkanes
1,1-Dimetalloalkanes obtained by the allylzincation of alkenylmagnesium compounds react smoothly with various functionalized alkylidenemalonates providing functionalized Z-olefins in good yields. If dimenthyl alkylidenemalonates are used, then excellent stereoselectivities are observed (92:8 to 100:0). An application to a short stereospecific synthesis of an insect pheromone [(Z)-7-dodecenyl acetate] is described (> 99.9% Z, 70% overall yield).
Tucker,Knochel
p. 530 - 536
(2007/10/02)
The Olefination of Functionalized Alkylidenemalonates by 1,1-Dimetalloalkanes: A New Chemo- and Stereoselective Preparation of Functionalized Olefins
The polyfunctional alkylidenemalonates 1, readily prepared by an addition-elimination reaction of FG-RCu(CN)ZnI to malonates of type 7, were found to undergo a highly chemoselective and stereoselective olefination reaction with 1,1-dimetalloalkanes of zinc and magnesium.An application to the stereospecific preparation of an insect pheromone 8 is reported.
Tucker, Charles E.,Rao, S. Achyutha,Knochel, Paul
p. 5446 - 5448
(2007/10/02)
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