144370-33-2Relevant articles and documents
Highly functionalized donor-acceptor cyclopropanes applied toward the synthesis of the Melodinus alkaloids
Goldberg, Alexander F.G.,Craig, Robert A.,O'Connor, Nicholas R.,Stoltz, Brian M.
supporting information, p. 2983 - 2990 (2015/05/27)
Abstract A series of highly substituted vinylcyclopropanes were prepared and examined as reaction partners in a palladium-catalyzed (3+2) cycloaddition with nitrostyrenes. Described herein are our efforts to synthesize an elusive 1,1-divinylcyclopropane by several distinct approaches, and to apply surrogates of this fragment toward the synthesis of the Melodinus alkaloids.
Baylis-Hillman reaction under solvent-free conditions - Remarkable rate acceleration and yield enhancement
Saikia, Monmi,Sarma, Jadab C.
experimental part, p. 1271 - 1276 (2011/02/24)
A simple and efficient method has been developed for remarkable rate acceleration and yield enhancement of the Baylis-Hillman reaction under solvent-free "neat conditions" and solvent-less isolation of products. Reaction of equimolar quantities of aldehyd
Auto-tandem catalysis: Facile synthesis of substituted alkylidenecyclohexanones by domino (4+2) cycloaddition-elimination reaction
Takasu, Kiyosei,Tanaka, Toru,Azuma, Takumi,Takemoto, Yoshiji
scheme or table, p. 8246 - 8248 (2010/12/20)
A catalytic domino reaction producing substituted 2-alkylidenecyclohexanone from 3-oxymethyl-2-siloxy-1,3-butadienes, which can be prepared from Baylis-Hillman adducts, and α,β-unsaturated ketones is described. The process involves two mechanistically dis
Octanol-accelerated Baylis-Hillman reaction
Park, Kwang-Su,Kim, Jinyoung,Choo, Hyunah,Chong, Youhoon
, p. 395 - 398 (2008/01/03)
The Baylis-Hillman reaction was greatly accelerated by use of octanol as an additive. Under the octanol-accelerated Baylis-Hillman conditions, unactivated aldehydes such as aliphatic aldehydes and aromatic aldehydes with electron-withdrawing substituents
Stereoselective synthesis of methyl 7-dihydro-trioxacarcinoside B
Koenig, Christian M.,Harms, Klaus,Koert, Ulrich
, p. 4777 - 4779 (2008/03/15)
(Chemical Equation Presented) A stereoselective synthesis of 7-dihydro-triocacarcinose B, a branched octose from the quinocyclines, has been achieved. The biocatalytic resolution of a Baylis-Hillman adduct and a subsequent ring-closing metathesis were use
Reaction of a cyclic oxosulfonium ylide with acetates of the Baylis-Hillman adducts: Tandem Michael - Intramolecular Corey-Chaykovsky reactions
Akiyama, Hitoshi,Fujimoto, Tetsuya,Ohshima, Katsuyoshi,Hoshino, Kenji,Yamamoto, Iwao,Iriye, Ryozo
, p. 427 - 430 (2008/02/12)
(equation presented) The reaction of the five-membered cyclic oxosulfonium ylide 2 with α-methylene-β-acetoxy ketones in the presence of two equimolar amounts of base afforded the cycloheptene oxide derivatives with stereoselectivity in 19-74% yield via a
Stereoselective epoxidation of hydroxyenones. The synthesis of the sidechain of clerocidin
Bailey,Marko,Ollis,Rasmussen
, p. 4509 - 4512 (2007/10/02)
The sidechains of clerocidin 1 and terpentecin 2 contain a unique chiral assembly [C5H5O4]. Models for the stereospecific synthesis of this structural feature are reported.
Nucleophile-Catalysed Additions of Aldehydes and Ketones to Acrylic Compounds: The Effectiveness of High Pressures
Hill, Jon S.,Isaacs, Neil S.
, p. 2641 - 2676 (2007/10/02)
The preparation of a wide range of compounds of general type: CH2=C(Z)-CR1R2OH (Z = CN, COOR, CHO,; R1,R2 = H, alkyl, aryl) from the reaction of CH2=CHZ with aldehydes and ketones, is effectively catalysed by tertiary amines especially DABCO.Rates are found to be very strongly accelerated by high pressures (2-10 kbar) which alone permits the additions of ketones or of crotonic acid derivatives to take place.In the absence of carbonyl acceptors novel oligomers of acrylic compounds form.
SYNTHESIS OF 3-HYDROXY-2-METHYLENE CARBONYL COMPOUNDS - EFFECT OF CATALYST AND SUBSTRATE ON REACTION RATE
Drewes, Siegfried E.,Freese, Susan D.,Emslie, Neville D.,Roos, Gregory H. P.
, p. 1565 - 1572 (2007/10/02)
3-Hydroxyquinuclidine enhances the rate of formation of the title compounds whereas the acetylated derivative is a poor catalyst.A comparative study shows that methyl vinyl ketone is more reactive than methyl acrylate in the Baylis-Hillman reaction.
