39178-64-8Relevant articles and documents
Stereoselective preparation of functionalized acyclic alkenylmagnesium reagents using i-PrMgCl-LiCl
Ren, Hongjun,Krasovskiy, Arkady,Knochel, Paul
, p. 4215 - 4217 (2007/10/03)
(Chemical Equation Presented) Acyclic functionalized alkenyl iodides are converted with high stereoselectivity to the corresponding functionalized alkenylmagnesium derivatives by the reaction with i-PrMgCl-LiCl between -40 and -20°C. Functional groups such as a nitrile, chloride, iodide, and ester are readily tolerated. The conversion of an alkenyl iodide bearing a keto group to the corresponding silylated cyanohydrin allows preparation of the corresponding Grignard reagent affording, after acylation and deprotection, unsaturated 1,4-diketones.
ALDOL REACTION OF ALLENOLATES GENERATED VIA 1,4-ADDITION OF IODIDE ANION OR ITS EQUIVALENT TO α,β-ACETYLENIC KETONES
Taniguchi, Mikio,Hino, Tohru,Kishi, Yoshito
, p. 4767 - 4770 (2007/10/02)
TMSI, Et2AlI, and (n-Bu)4NI/TiCl4 smoothly added to α,β-acetylenic ketones in a 1,4-fashion to yield allenolates 2, which reacted with aldehydes providing aldol adducts in good overall yield.A high Z-stereoselectivity was achieved by use of (n-Bu)4NI/TiCl4 at -78 deg C, while a high E-stereoselectivity occured at 0 deg C.