- Highly functionalized donor-acceptor cyclopropanes applied toward the synthesis of the Melodinus alkaloids
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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.
- Goldberg, Alexander F.G.,Craig, Robert A.,O'Connor, Nicholas R.,Stoltz, Brian M.
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supporting information
p. 2983 - 2990
(2015/05/27)
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- Baylis-Hillman reaction under solvent-free conditions - Remarkable rate acceleration and yield enhancement
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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
- Saikia, Monmi,Sarma, Jadab C.
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experimental part
p. 1271 - 1276
(2011/02/24)
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- Auto-tandem catalysis: Facile synthesis of substituted alkylidenecyclohexanones by domino (4+2) cycloaddition-elimination reaction
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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
- Takasu, Kiyosei,Tanaka, Toru,Azuma, Takumi,Takemoto, Yoshiji
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scheme or table
p. 8246 - 8248
(2010/12/20)
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- Octanol-accelerated Baylis-Hillman reaction
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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
- Park, Kwang-Su,Kim, Jinyoung,Choo, Hyunah,Chong, Youhoon
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p. 395 - 398
(2008/01/03)
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- Stereoselective synthesis of methyl 7-dihydro-trioxacarcinoside B
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(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
- Koenig, Christian M.,Harms, Klaus,Koert, Ulrich
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p. 4777 - 4779
(2008/03/15)
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- Reaction of a cyclic oxosulfonium ylide with acetates of the Baylis-Hillman adducts: Tandem Michael - Intramolecular Corey-Chaykovsky reactions
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(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
- Akiyama, Hitoshi,Fujimoto, Tetsuya,Ohshima, Katsuyoshi,Hoshino, Kenji,Yamamoto, Iwao,Iriye, Ryozo
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p. 427 - 430
(2008/02/12)
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- Stereoselective epoxidation of hydroxyenones. The synthesis of the sidechain of clerocidin
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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.
- Bailey,Marko,Ollis,Rasmussen
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p. 4509 - 4512
(2007/10/02)
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- Nucleophile-Catalysed Additions of Aldehydes and Ketones to Acrylic Compounds: The Effectiveness of High Pressures
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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.
- Hill, Jon S.,Isaacs, Neil S.
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p. 2641 - 2676
(2007/10/02)
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- SYNTHESIS OF 3-HYDROXY-2-METHYLENE CARBONYL COMPOUNDS - EFFECT OF CATALYST AND SUBSTRATE ON REACTION RATE
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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.
- Drewes, Siegfried E.,Freese, Susan D.,Emslie, Neville D.,Roos, Gregory H. P.
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p. 1565 - 1572
(2007/10/02)
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- A New Synthesis of Functionalized 6,8-Dioxabicyclooctanes
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Functionalized 6,8-dioxabicyclooctanes are prepared efficiently in two steps from aldehydes and methyl vinyl ketone.
- Daude, Norbert,Eggert, Ulrike,Hoffmann, H. M. R.
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p. 206 - 207
(2007/10/02)
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- FUNCTIONALISATION OF THE α POSITION OF ACRYLATE SYSTEMS BY THE ADDITION OF CARBONYL COMPOUNDS: HIGHLY PRESSURE-DEPENDENT REACTIONS.
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Aldehydes and ketones will add to acrylonitrile, acrylate esters, acrolein and α, β,-enones with the formation of a range of 2(X)-propen-1-ols (X= CN, COOR, COR).The reactions are catalysed by tertiary amines and are very sensitive to pressure.A wide vari
- Hill, Jonathan S.,Isaacs, Neil S.
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p. 5007 - 5010
(2007/10/02)
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- Aldol Reaction of Aluminium Enolate Resulting from 1,4-Addition of R2AlX to α,β-Unsaturated Carbonyl Compound. A 1-Acylethenyl Anion Equivalent
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Organoaluminium reagents R2AlX (X=SPh, SeMe) easily add to α,β-unsaturated carbonyl compounds in 1,4-fashion.The resulting aluminium enolates react with aldehydes to give aldol adducts in fair to good yields.Formal elimination of HX from the adducts provi
- Itoh, Akira,Ozawa, Shuji,Oshima, Koichiro,Nozaki, Hitosi
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p. 274 - 278
(2007/10/02)
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- ALDOL REACTION OF ALUMINIUM ENOLATE RESULTING FROM 1,4-ADDITION OF Me2AlSPh TO α,β-UNSATURATED CARBONYL COMPOUND. A 1-ACYLETHENYL ANION EQUIVALENT
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Me2AlSPh or Me2AlSeMe adds to α,β-unsaturated carbonyl compounds in 1,4-fashion.The resulting aluminium enolates react with aldehydes effectively to afford the adducts of the title anion after formal PhSH (or MeSeH)-elimination
- Itoh, Akira,Ozawa, Shuji,Oshima, Koichiro,Nozaki, Hitosi
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p. 361 - 364
(2007/10/02)
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