66869-17-8Relevant academic research and scientific papers
Organocatalyzed Tsuji-Trost reaction: a new method for the closure of five- and six-membered rings
Vulovic, Bojan,Bihelovic, Filip,Matovic, Radomir,Saicic, Radomir N.
supporting information; experimental part, p. 10485 - 10494 (2010/02/28)
A combination of organotransition metal catalysis and organocatalysis allows for Tsuji-Trost 5-exo- and 6-exo-cyclizations of aldehydes. This transformation can also be accomplished as a catalytic asymmetric reaction, which affords vinylcyclopentane deriv
Multicatalytic synthesis of complex tetrahydrofurans involving bismuth(iii) triflate catalyzed intramolecular hydroalkoxylation of unactivated olefins
Kelly, Brendan D.,Allen, Julia M.,Tundel, Rachel E.,Lambert, Tristan H.
supporting information; experimental part, p. 1381 - 1383 (2009/10/02)
A multicatalytic synthesis of complex tetrahydrofurans has been developed involving a Bi(OTf)3-catalyzed nucleophilic addition/ hydroalkoxylation sequence. Complex tetrahydrofuranyl products may be formed rapidly in high yield and with good diastereoselectivity. The demonstrated scope of hydroalkoxylation has also been expanded to include substrates bearing useful functional handles including carboxylate ester, olefin, nitrile, and nitro groups.
Organocatalyzed cyclizations of π-allylpalladium complexes: A new method for the construction of five- and six-membered rings
Bihelovic, Filip,Matovic, Radomir,Vulovic, Bojan,Saicic, Radomir N.
, p. 5063 - 5066 (2008/03/28)
Synergic combination of organotransition metal catalysis and organocatalysis allows, for the first time, the Tsuji-Trost cyclization of aldehydes. A catalytic asymmetric variant of the reaction is also possible.
Synthesis of eleven-membered carbocycles via a homo-Cope type of five-carbon ring expansion reaction utilized β-(hydroxymethyl)allylsilane
Suzuki, Hideyuki,Kuroda, Chiaki
, p. 3157 - 3174 (2007/10/03)
Eleven-membered carbocycles were synthesized from six-membered compounds fitted with a β-(hydroxymethyl)allylsilane unit via the title reaction. Namely, trans- and cis-(E)-2-(trimethylsilylmethyl)-3-(2-vinylcyclohex-1-yl)prop-2-en-1-ol were treated with Tf2O in CH2Cl2 in the presence of 2,6-lutidine to afford (1E)-3-methylenecycloundeca-1,6-diene in good yield. The geometry of the product was shown to depend upon the trans- and cis-substitution pattern on the cyclohexane ring of the substrates; i.e. trans-isomer afforded (6E)-product exclusively and cis-isomer afforded the mixture of (6E)- and (6Z)-product in 1:2 ratio. The (Z)-substrate with respect to allylsilane moiety afforded the same ring expansion product, however, the yield was lower than the reaction with the (E)-substrate. The substrates bearing t-butyl or benzyloxy substituents on the cyclohexane ring also afforded the product analogously, indicating that the reaction depends upon the conformation of the substrate. On the other hand, the substrate bearing isopropenyl group instead of a simple vinyl group did not afford the ring expansion product but produced bicyclo[5.4.0]undecane via the ene reaction.
(E)-selective synthesis of γ-substituted-β -(ethoxycarbonyl)allylsilanes utilising ethyl 2-diphenylphosphono-3-(trimethylsilyl)propionate. Improved synthesis of 11 membered carbocycle by a homo-Cope reaction
Suzuki, Hideyuki,Kuroda, Chiaki
, p. 310 - 312 (2007/10/03)
(E)-γ-Substituted-β-(ethoxycarbonyl)allylsilanes were selectively synthesised by Horner-Wadsworth-Emmons reaction utilising ethyl 2-diphenylphosphono-3-(trimethylsilyl)propionate.
Synthesis of eleven-membered carbocycles by a new five-carbon ring expansion reaction
Suzuki, Hideyuki,Monda, Akiko,Kuroda, Chiaki
, p. 1915 - 1917 (2007/10/03)
3-Methylenecycloundeca-1,6-diene was synthesized by a homo-Cope ring expansion reaction of 2-(trimethylsilylmethyl)-3-(2-vinylcyclohexyl)prop-2-en-1-ol.
Novel nitrile oxide cycloaddition approach towards papuamine: Stereoselective synthesis of a potentially useful trans-hydrindane intermediate
Saha, Arabinda,Bhattacharjya, Anup
, p. 495 - 496 (2007/10/03)
In a potentially useful approach to the marine alkaloid papuamine 1, a known trans-hydrindane intermediate 17 has been synthesised in racemic form using a model sequence of reactions involving a nitrile oxide cycloaddition as a key step.
