126741-70-6Relevant academic research and scientific papers
Gold(i)-catalyzed pathway-switchable tandem cycloisomerizations to indolizino[8,7-: B] indole and indolo[2,3-a] quinolizine derivatives
Liu, Chengjun,Sun, Zenghui,Xie, Fukai,Liang, Guoduan,Yang, Lu,Li, Yaqiao,Cheng, Maosheng,Lin, Bin,Liu, Yongxiang
supporting information, p. 14418 - 14421 (2019/12/05)
Experimental and theoretical explorations were performed on the pathways of the cascade cycloisomerizations of tryptamine-N-ethynylpropiolamide substrates. The methodology provided a common strategy to access either indolizino[8,7-b]indoles or indolo[2,3-
Synthesis and Isolation of Organogold Complexes through a Controlled 1,2-Silyl Migration
McGee, Philippe,Bellavance, Gabriel,Korobkov, Ilia,Tarasewicz, Anika,Barriault, Louis
supporting information, p. 9662 - 9665 (2015/06/30)
During our efforts toward the synthesis of naturally occurring polyprenylated polycyclic acylphloroglucinol using a AuI-catalyzed 6-endo dig carbocyclization, we isolated stable vinyllic gold intermediates. Optimization lead to isolated yields of up to 98 %, using 2-(di-tert-butylphosphino)biphenyl as the ligand. This transformation is derived from a silyl rearrangement that can be fully controlled according to the nature of the substituent on the ynone. This selective transformation does not require basic conditions to prevent protodeauration. These vinylgold complexes are the first isolated intermediates during a silyl migration with gold(I). More than 16 new organogold complexes were synthesized and characterized by single-crystal X-ray diffraction. Reactivity of these complexes is also presented.
Reactivity pattern of bis(propargyloxy) disulfides: Tandem rearrangements and cyclizations
Braverman, Samuel,Pechenick-Azizi, Tatiana,Gottlieb, Hugo E.,Sprecher, Milon
experimental part, p. 1741 - 1750 (2011/07/09)
Thirty-five substituted bis(propargyloxy) disulfides were successfully prepared in good to excellent yields, and their reactivity was found to be strongly dependent on the substitution pattern of the reactant. Inter alia they undergo surprising tandem sigmatropic rearrangements and cycloadditions. Three heretofore unknown product types were isolated and fully characterized: 6,7-dithiabicyclo[3.1.1]heptan-2-one 6-oxide derivatives, two isomeric 1,2-dithiete 1,1-dioxides (α,β-unsaturated four-membered cyclic thiosulfonates) from bis(propargyloxy) disulfides with α- or γ-alkyl-substituted propargyl groups, and two isomeric 2-oxa-5,7-dithiabicyclo[2.2.1]heptane 5-oxides from bis(propargyloxy) disulfides with α-tert-butyl- or α,α-dialkyl-substituted propargyl groups. Georg Thieme Verlag Stuttgart - New York.
Improved method for the synthesis of β-carbonyl silyl-1,3-dithianes by the double conjugate addition of 1,3-dithiol to propargylic carbonyl compounds
Mukherjee, Sumit,Kontokosta, Dimitra,Patil, Aditi,Rallapalli, Sivakumar,Lee, Daesung
supporting information; experimental part, p. 9206 - 9209 (2010/03/02)
(Chemical Equation Presented) Base-mediated double conjugate addition of 1,3-propane dithiol to various silylated propargylic aldehydes and ketones allows for an efficient and scalable synthesis of β-carbonyl silyl-1,3-dithianes.
Reaction of δ-silyl-γ,δ-epoxy-α,β-unsaturated acylsilanes with cyanide ion: Possibility of the formation of silicate intermediate in anion-induced ring opening of epoxysilanes
Tanaka, Koudai,Masu, Hyuma,Yamaguchi, Kentaro,Takeda, Kei
, p. 6429 - 6432 (2007/10/03)
Reaction of trans- and cis-δ-silyl-γ,δ-epoxy-α, β-unsaturated acylsilanes 1 and 9 with cyanide ion in the presence of an electrophile affords double Brook rearrangement products 10 in an E/Z ratio depending on the cis/trans geometry of the epoxysilanes.
Tandem Base-Promoted Ring-Opening/Brook Rearrangement/Allylic Alkylation of O-Silyl Cyanohydrins of β-Silyl-α,β-epoxyaldehyde: Scope and Mechanism
Sasaki, Michiko,Kawanishi, Eiji,Nakai, Yoshio,Matsumoto, Tatsuya,Yamaguchi, Kentaro,Takeda, Kei
, p. 9330 - 9339 (2007/10/03)
Metalated O-silyl cyanohydrins of β-silyl-α,β -epoxyaldehyde have been found to serve as functionalized homoenolate equivalents by a tandem sequence involving base-promoted ring opening of the epoxide, Brook rearrangement, and alkylation of the resulting
Stereocontrolled synthesis of α-trialkylsilyl-β,γ-unsaturated aldehydes via palladium (0) catalysis synthetic usefulness
Le Bideau,Gilloir,Nilsson,Aubert,Malacria
, p. 7487 - 7510 (2007/10/03)
The reaction of silicon substituted vinyloxiranes in the presence of catalytic amount of palladium (0) catalyst affords the title compounds. This new reaction proceeds smoothly, under very mild conditions and with complete chirality transfer. One-pot addition of selected organometallic nucleophiles to these aldehydes at very low temperature led to a highly selective preparation of the corresponding alcohols in very good yields. Influence of substituents on the silicon atom and of the ligands of palladium have been studied.
The Stereochemistry of Organometallic Compounds. XXXIV. Regioselection in the Hydroformylation of Silylalkenes
Doyle, M. Michael,Jackson, W. Roy,Perlmutter, Patrick
, p. 1907 - 1918 (2007/10/02)
The regiochemistry of hydroformylation of alkenes can be controlled by use of bulky silyl groups attached to the alkene.Use of the t-butyldiphenylsilyl group leads to almost total regiocontrol and the method has been applied to the synthesis of aldols.
