155886-13-8Relevant articles and documents
Unsaturated fatty alcohol derivatives as a source of substituted allylzirconocene
Chinkov, Nicka,Levin, Anat,Marek, Ilan
, p. 465 - 468 (2007/10/03)
(Chemical Equation Presented) From A to Z: Allylzirconocenes have been easily prepared in a one-pot procedure through a tandem allylic C-H activation-β-elimination reaction from unsaturated fatty alcohol and ether starting materials (see scheme). The reaction proceeds rapidly under mild condition and is insensitive to the length of the carbon tether between the double bond and the alcohol moiety.
Allylbarium reagents: Unprecedented regio- and stereoselective allylation reactions of carbonyl compounds
Yanagisawa, Akira,Habaue, Shigeki,Yasue, Katsutaka,Yamamoto, Hisashi
, p. 6130 - 6141 (2007/10/02)
The first direct preparation of allylbarium reagents by reaction of in situ generated reactive barium with various allylic chlorides and their new and unexpected selective allylation reactions with carbonyl compounds are disclosed. Highly reactive barium was readily prepared by the reduction of barium iodide with 2 equiv of lithium biphenylide in dry THF at room temperature. A variety of carbonyl compounds reacted with barium reagents generated from (E)- or (Z)-allylic chlorides in THF at -78 °C. All reactions resulted in high yields with remarkable α-selectivities not only with aldehydes but also with ketones. The double bond geometry of the starting allylic chloride was completely retained in each case. Stereochemically homogeneous (E)- and (Z)-β,γ-unsaturated carboxylic acids were easily prepared in good yields by highly α-selective carboxylation of allylic barium reagents with carbon dioxide. A selective Michael addition reaction with α,β-unsaturated cycloalkanone was also achieved using an allylbarium reagent. Treatment of 2-cyclopentenone (1 equiv) with allylbarium chloride (2 equiv) in THF at -78 °C for 20 min afforded 3-allylcyclopentanone in 94% yield with a 1,4/1,2 ratio of >99/1. Furthermore, the in situ generated barium enolate was efficiently trapped with various kinds of electrophiles (Me2C=CHCH2Br, nC5H11CHO, and CH3COCl).
Charge Reversal of Electrophilic ?-Allylpalladium Intermediates: Carbonyl Allylation bu Allylic Acetates with Pd(PPh3)4-Zn
Masuyama, Yoshiro,Kinugawa, Nobuyoshi,Kurusu, Yasuhiko
, p. 3702 - 3704 (2007/10/02)
Allylic acetates were reduced by zinc in the presence of a catalytic amount of Pd(PPh3)4 to serve as nucleophilic allylating agents, which reacted with aldehydes to afford the corresponding homoallylic alcohols.
