127015-48-9Relevant academic research and scientific papers
Reversal of Chemoselectivity in Organotin Lewis Acid-Catalyzed Reaction of Ketene Silyl Acetal with Aldehyde and α-Enal
Chen, Jianxie,Otera, Junzo
, p. 29 - 30 (1997)
The organotin Lewis acid-catalyzed reaction of ketene silyl acetal with aldehydes results in reversal of chemoselectivity: α-enals react preferentially or exclusively in competition with an alkanal or even aromatic aldehydes.
Cooperative organocatalysis of Mukaiyama-type aldol reactions by thioureas and nitro compounds
Bukhryakov, Konstantin V.,Desyatkin, Victor G.,Rodionov, Valentin O.
, p. 7576 - 7579 (2016)
A unique organocatalytic system for Mukaiyama-type aldol reactions based on the cooperative action of nitro compounds and thioureas has been identified. This system is compatible with a wide range of substrates and does not require low temperatures, inert atmospheres, or an aqueous workup. A catalytic mechanism based on nitro group-mediated silyl cation transfer has been proposed.
Turnagainolides A and B, cyclic depsipeptides produced in culture by a Bacillus sp.: Isolation, structure elucidation, and synthesis
Li, Dehai,Carr, Gavin,Zhang, Yonghong,Williams, David E.,Amlani, Ashraf,Bottriell, Helen,Mui, Alice L.-F.,Andersen, Raymond J.
experimental part, p. 1093 - 1099 (2011/08/03)
Two new cyclic depsipeptides, turnagainolides A (1) and B (2), have been isolated from laboratory cultures of a marine isolate of Bacillus sp. The structures of 1 and 2, which are simply epimers at the site of macrolactonization, were elucidated by analysis of NMR data and chemical degradation. A total synthesis of the turnagainolides confirmed their structures. Turnagainolide B (2) showed activity in a SHIP1 activation assay. (Chemical Equation Presented).
The β-lactone route to α,β-unsaturated δ-lactones. Total syntheses of (±)-goniothalamin and (-)-massoialactone
Fournier, Lycia,Kocienski, Philip,Pons, Jean-Marc
, p. 1659 - 1663 (2007/10/03)
The HF-induced translactonization of 2′-silyloxy-3-trimethylsilyl-2- oxetanones, obtained through Lewis acid-promoted [2+2] cycloaddition between β-silyloxyaldehydes and trimethylsilylsilylketene, into α,β-unsaturated δ-lactones is applied to the syntheses of (±)-goniothalamin and (-)-massoialactone.
Substituent effects on the stereochemical course of electrophile- initiated tetrahydropyran-forming reactions: A possible stereoelectronic effect
Hart, David J.,Patterson, Suzanne,Zakarian, Alain
, p. 1025 - 1028 (2007/10/03)
A series of 4-penten-1,3-diol derivatives were prepared and treated with phenylselenenyl chloride to provide tetrahydropyrans. The stereochemical course of the reactions is consistent with a chair-like transition state in which the oxygen substituent at the 3-position largely occupies an axial site. A structurally related 3-methyl-4-penten-1-ol derivative gave a major product consistent with a chair transition state in which the methyl group occupies an equatorial site.
Organotin perchlorates as gentle Lewis acid catalysts in Mukaiyama reaction
Chen, Jian-Xie,Otera, Junzo
, p. 14275 - 14286 (2007/10/03)
Organotin perchlorates catalyze Mukaiyama reaction of ketene silyl acetal in highly chemoselective but uncommon manners. The competition reaction between aldehyde and acetal leads to exclusive formation of the aldehyde aldols leaving the acetal counterpar
oxotitanium. A Chemoselective and Efficient Catalyst for Aldol-type Reaction of Ketene Silyl Acetals with Aldehydes
Hara, Ryuichiro,Mukaiyama, Teruaki
, p. 1909 - 1912 (2007/10/02)
In the presence of catalytic amount of oxotitanium, ketene silyl acetals smoothly react with aldehydes to afford the corresponding β-hydroxy carboxylic esters in good yields under mild conditions.According to this procedure, a
