(Z)-α-(Trimethylsilyl) α,β-Unsaturated Esters. Their Stereoselective Conversion into α,β- and β,γ-Unsaturated Esters and β,γ-Unsaturated Ketene Acetals
Deprotonation of methyl (Z)-α-(trimethylsilyl) α,β-unsaturated esters with lithium diisopropylamide (LDA) or with lithium hexamethyldisilazide (LHMDS) in the presence of hexamethylphosphoramide (HMPA) as an activator, followed by protonation of the interm
Najafi, M. Ramin,Wang, Mei-Ling,Zweifel, George
p. 2468 - 2476
(2007/10/02)
A CONVENIENT STEREOSPECIFIC SYNTHESIS OF α,β-UNSATURATED CARBOXYLIC ESTERS VIA THE PALLADIUM-CATALYZED CARBONYLATION OF 1-ALKENYLBORANES
1-Alkenylboranes readily prepared by the hydroboration of alkynes react smoothly with carbon monoxide in the presence of palladium chloride and sodium acetate in methanol to give the corresponding α,β-unsaturated carboxylic esters with retention of configuration with respect to alkenylboranes in good yields.
Miyaura, Norio,Suzuki, Akira
p. 879 - 882
(2007/10/02)
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