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| - Mechanistic Studies on the Heck−Mizoroki Cross-CouplingReaction of a Hindered Vinylboronate Ester as a Key Approach toDeveloping a Highly Stereoselective Synthesis of a C1−C7Z,Z,E-Triene Synthon for Viridenomycin
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| - Mechanistic studies of the Heck−Mizoroki reaction of a vinylboronate ester with electronically different(four-substituted) aryl iodides shows that electron donors accelerate the cross-coupling, demonstratingthat the oxidative addition step is not rate determining and that there is development of some degree ofpositive charge in the rate determining step. These results were used as a basis to allow the developmentof reaction conditions for the Heck−Mizoroki coupling of a hindered vinylboronate ester with electrondeficient methyl cis-2-iodoacrylate. The resulting dienylboronate ester was converted through a series ofhighly stereoselective iodo-deboronations and Heck−Mizoroki reactions into a trienyl iodide precursorfor further application in the total synthesis of viridenomycin.
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