86342-79-2Relevant articles and documents
Mild TiIII- and Mn/ZrIV-catalytic reductive coupling of allylic halides: Efficient synthesis of symmetric terpenes
Barrero, Alejandro F.,Herrador, M. Mar,Quilez Del Moral, Jose F.,Arteaga, Pilar,Arteaga, Jesus F.,Dieguez, Horacio R.,Sanchez, Elena M.
, p. 2988 - 2995 (2007/10/03)
(Chemical Equation Presented) Two new efficient methods for the regioselective homocoupling of allylic halides using either catalytic Ti III or the combination Mn/ZrIV catalyst have been developed. The regio- and stereoselectivity of the process proved to increase significantly when the Mn/ZrIV catalyst is used as the coupling reagent and when cyclic substituted allylic halides are used as substrates. The use of Lewis acids such as collidine hydrochloride allowed the quantity of catalyst to be lowered up to 0.05 equiv. We have proved the utility of these protocols with the synthesis of different terpenoids such as (+)-β-onoceradiene (1), (+)-β-onocerine (2), squalene (5), and advanced key-intermediates in the syntheses of (+)-cymbodiacetal (3) and dimeric ent-kauranoids as xindongnin M (4a).
Highly Selective Homocoupling Reaction of Allylic Halides Using Barium Metal
Yanagisawa, Akira,Hibino, Hiroaki,Habaue, Shigeki,Hisada, Yoshiyuki,Yamamoto, Hisashi
, p. 6386 - 6387 (2007/10/02)
The highly α,α' selective and stereocontrolled homocoupling reaction of allylic halides was achieved using barium reagent.The double-bond geometry of the starting allylic chloride was completely retained. α,α' Cross-coupling products were also prepared stereospecifically and regioselectively by this method.
PALLADIUM-CATALYZED COUPLING OF ALLYLIC ACETATES WITH ZINC
Sasaoka, Shin-ichi,Yamamoto, Taku,Kinoshita, Hideki,Inomata, Katsuhiko,Kotake, Hiroshi
, p. 315 - 318 (2007/10/02)
Allylic acetates were coupled with zinc dust in the presence of a catalytic amount of to give the corresponding 1,5-dienes under mild conditions in high yields.Significant cosolvent effects were found with methanol or 1,2-ethanediol in tetrahydrofuran.