96694-03-0Relevant articles and documents
Chiral phosphine oxide BINAPO as a catalyst for enantioselective allylation of aldehydes with allyltrichlorosilanes
Nakajima, Makoto,Kotani, Shunsuke,Ishizuka, Tadao,Hashimoto, Shunichi
, p. 157 - 159 (2005)
The effectiveness of chiral phosphine oxide BINAPO as a catalyst for the enantioselective addition of allyltrichlorosilanes to aldehydes was demonstrated, wherein the combination of diisopropylethylamine and tetrabutylammonium iodide as additives is cruci
Enantioselective Synthesis of Isoxazolines Enabled by Palladium-Catalyzed Carboetherification of Alkenyl Oximes
Chen, Mingjie,Li, Wenbo,Wang, Lei,Wang, Yuzhuo,Zhang, Junliang,Zhang, Kenan
supporting information, p. 4421 - 4427 (2020/02/11)
Reported here is a highly efficient Pd/Xiang-Phos catalyzed enantioselective carboetherification of alkenyl oximes with either aryl or alkenyl halides, delivering various chiral 3,5-disubstituted and 3,5,5-trisubstituted isoxazolines in good yields with u
Enantioselective Conjunctive Cross-Coupling of Bis(alkenyl)borates: A General Synthesis of Chiral Allylboron Reagents
Edelstein, Emma K.,Namirembe, Sheila,Morken, James P.
supporting information, p. 5027 - 5030 (2017/05/04)
Palladium-catalyzed conjunctive cross-coupling is used for the synthesis of enantioenriched allylboron reagents. This reaction employs nonsymmetric bis(alkenyl)borates as substrates and appears to occur by a mechanism that involves selective activation of the less substituted alkene followed by migration of the more substituted alkene during the course of a Pd-induced metalate rearrangement.
Catalytic, nucleophilic allylation of aldehydes with 2-substituted allylic acetates: Carbon-carbon bond formation driven by the water-gas shift reaction
Denmark, Scott E.,Matesich, Zachery D.
, p. 5970 - 5986 (2014/07/21)
The ruthenium-catalyzed allylation of aldehydes with allylic acetates has been expanded to incorporate substituents at the 2-position of the allylic components. Allylic acetates bearing a variety of substituents (CO 2-t-Bu, COMe, Ph, CH(OEt)su
Allyl-, allenyl-, and propargyl-transfer reactions through cleavage of C-C bonds catalyzed by an n-heterocyclic carbene/copper complex: Synthesis of multisubstituted pyrroles
Sai, Masahiro,Yorimitsu, Hideki,Oshima, Koichiro
supporting information; scheme or table, p. 3294 - 3298 (2011/06/21)
Cat. in the bag: The pictured copper complex can promote C-C bond cleavage through retro-allylation of homoallyl alcohols to form allylcopper species. This process is applicable to catalytic allylation of aldehydes and imines with homoallyl alcohols. The method has also been extended to regioselective allenylation and propargylation of imines. Copyright
On the mechanism of carbohydroxypalladation of enynes. Additional insights on the cyclization of enynes with electrophilic metal complexes
Nevado, Cristina,Charruault, Lise,Michelet, Veronique,Nieto-Oberhuber, Cristina,Paz Munoz,Mendez, Maria,Rager, Marie-Noelle,Genet, Jean-Pierre,Echavarren, Antonio M.
, p. 706 - 713 (2007/10/03)
Different mechanisms have been proposed for the cyclization of enynes catalyzed by electrophilic metal halides or complexes. We present evidence to indicate that the previously reported "carbohydroxypalladation" and the "hydroxycyclization catalyzed by PtII" are closely related reactions. Thus, palladium complexes formed in situ from PdCl2 and trisulfonated phosphane TPPTS or cyclic phosphite P(OCH2)3CEt as the ligands catalyze the methoxy- or hydroxycyclization of enynes with selectivities similar to those observed with PtII complexes. Deuteration studies indicate that activation of the alkyne by PdII promotes an anti-addition of the alkene. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Indium mediated allylation and propargylation reactions of dimethyl acetals and ketals
Kwon, Jin Sun,Pae, Ae Nim,Choi, Kyung Il,Koh, Hun Yeong,Kim, Youseung,Cho, Yong Seo
, p. 1957 - 1959 (2007/10/03)
Indium mediated allylation and propargylation reactions of acetals and ketals with various allyl or propargyl bromides in aqueous media successfully provided the corresponding homoallylic or homopropargylic (and allenylic) alcohol, respectively, in moderate to good yields. Highly chemoselective allylation is also described. The ketal and aryl acetal could be selectively allylated over the aliphatic one in 80-84% yields.
Facile and Highly Stereoselective Synthesis of Homoallylic Alcohols Using Organosilicon Intermediates
Kobayashi, Shu,Nishio, Koichi
, p. 6620 - 6628 (2007/10/02)
Allyltrichlorosilanes regioselectively reacted with aldehydes in N,N-dimethylformamide (DMF) without a catalyst to afford the corresponding homoallylic alcohols in high yields.The reactions proceeded under neutral conditions, and syn- and anti-homoallylic alcohols were stereoselectively obtained from (Z)- and (E)-allyltrichlorosilanes, respectively.In these reactions, DMF coordinated to the silicon atom of the allyltrichlorosilanes to form hypervalent silicates, which in turn reacted with aldehydes smoothly.Solvent effects in these reactions were also examined.The reactions were applied to the one-pot synthesis of homoallylic alcohols from allylic chlorides via organosilicon intermediates.While syn-homoallylic alcohols were prepared from (Z)-allyl chlorides, anti-homoallylic alcohols were obtained from (E)-allyl chlorides.Unique regioselectivities in the reactions of 1-chloro-2,4-pentadiene were also found.Finally, the one-pot synthesis of homoallylic alcohols from 1,3-dienes is reported.
A New Type of Catalysis by Copper(I) Salts in the Barbier-type Aldehyde Allylation with Tin(II) Chloride. Short Syntheses of (+/-)-Lavandulol and its γ, δ-Dihydro Derivative
Imai, Toshiro,Nishida, Shinya
, p. 277 - 278 (2007/10/02)
Copper(I) halides and cyanide catalyse the Barbier-type aldehyde allylation with allylic bromides, chlorides or sulfonates and tin(II) chloride enabling the reaction to take place under very mild conditions with high efficiency.
