1076-66-0Relevant articles and documents
Iridium-catalyzed enantioselective allyl-allylsilane cross-coupling
Hamilton, James Y.,Hauser, Nicole,Sarlah, David,Carreira, Erick M.
, p. 10759 - 10762 (2014)
An enantioselective allyl-allylsilane cross-coupling involving racemic branched allylic alcohols and allylsilanes is reported. An iridium-(P,olefin) phosphoramidite complex enables the transformation with high regio- and stereoselectivity under operationally simple conditions. The utility of the coupling is demonstrated in a concise catalytic, enantioselective synthesis of a pyrethroid insecticide protrifenbute. Enantioselective allyl-allylsilane cross-coupling between branched racemic allylic alcohols and allylsilanes was developed. An Ir-(P,olefin) catalyst in conjunction with Sc(OTf)3 as the acidic promoter enables the preparation of chiral 1,5-dienes with up to 99 % ee. The described method was successfully applied to the asymmetric synthesis of the pyrethroid insecticide protrifenbute. cod=1,5-cyclooctadiene, Tf=trifluoromethanesulfonyl.
Cobalt- and rhodium-catalyzed cross-coupling reaction of allylic ethers and halides with organometallic reagents
Yasui, Hiroto,Mizutani, Keiya,Yorimitsu, Hideki,Oshima, Koichiro
, p. 1410 - 1415 (2006)
Reactions of 2-alkenyl methyl ether with phenyl, trimethylsilylmethyl, and allyl Grignard reagents in the presence of cobalt(II) complexes are discussed. The success of the reactions heavily depends on the combination of the substrate, ligand, and Grignard reagent. In the reaction of cinnamyl methyl ether, the formation of the linear coupling products predominates over that of the relevant branched products. In the cobalt-catalyzed allylation of allylic ethers, addition of a diphosphine ligand can change the regioselectivity, mainly providing the corresponding branched products. Rhodium complexes catalyze the reactions of allylic ethers and halides with allylmagnesium chloride and allylzinc bromide, respectively, in which the branched coupling product is the major product.
Iridium-Catalyzed Enantioselective Allyl-Allyl Cross-Coupling of Racemic Allylic Alcohols with Allylboronates
Zheng, Yu,Yue, Bei-Bei,Wei, Kun,Yang, Yu-Rong
supporting information, p. 8035 - 8038 (2019/01/14)
Carreira's iridium-(P, olefin) phosphoramidite-based catalytic system that allows asymmetric allyl-allylboronate cross-coupling with high enantioselectivity is reported. This transformation tolerates a large variety of racemic branched allylic alcohols an
Branched/linear selectivity in palladium-catalyzed allyl-allyl cross-couplings: the role of ligands
Ardolino, Michael J.,Morken, James P.
, p. 6409 - 6413 (2015/08/18)
Abstract While Pd-catalyzed allyl-allyl cross-couplings in the presence of small-bite-angle bidentate ligands reliably furnish the branched regioisomer with high levels of selectivity, cross-couplings in the presence of large-bite-angle bidentate ligands