184839-53-0Relevant academic research and scientific papers
Unique chemoselective Mukaiyama aldol reaction of silyl enol diazoacetate with aldehydes and acetals catalyzed by MgI2 etherate
Meng, Xiangwei,Pan, Haokun,Zhong, Tengjiang,Zhang, Xingxian
, (2019/10/28)
Functionalized diazo acetoacetates are prepared by an efficient Mukaiyama aldol reaction between 3-TBSO-2-diazo-3-butenoate with aldehydes and acetals under mild reaction conditions. A variety of substituted aldehydes and the corresponding acetals are both accessible in good to excellent yields through this methodology. MgI2 etherate (MgI2·(OEt2)n) is the preferred catalyst and, the addition proceeds without decomposition of the diazo moiety. In addition, this MgI2·(OEt2)n-catalyzed Mukaiyama aldol reaction shows unique chemoselectivity towards aldehydes and acetals.
Synthesis of the anti-HIV agent (-)-hyperolactone C by using oxonium ylide formation-rearrangement
Hodgson, David M.,Man, Stanislav
supporting information; experimental part, p. 9731 - 9737 (2011/10/05)
Starting from readily available (S)-styrene oxide an asymmetric synthesis is described of the naturally occurring anti-HIV spirolactone (-)-hyperolactone C, which possesses adjacent fully substituted stereocenters. The key step involves a stereocontrolled RhII-catalysed oxonium ylide formation-[2,3] sigmatropic rearrangement of an α-diazo-β-ketoester bearing allylic ether functionality. From the resulting furanone, an acid-catalysed lactonisation and dehydrogenation gives the natural product.
Aldol-cyclization reaction sequence for the synthesis of tetrahydrofurans
Calter, Michael A.,Sugathapala, Priyantha M.,Zhu, Cheng
, p. 3837 - 3840 (2007/10/03)
The aldol reactions of α-diazo-β-ketoesters with a variety of aldehydes produced adducts which underwent Rh(II)-catalyzed O-H insertion reaction to yield highly substituted tetrahydrofurans. Alkylation and decarboxylation of these tetrahydrofurans formed a wide variety of tetrahydrofuran structures.
Annelation of aromatic oxo compounds
Karady, Sandor,Amato, Joseph S.,Reamer, Robert A.,Weinstock, Leonard M.
, p. 8277 - 8280 (2007/10/03)
The silyl enol ether of α-diazoacetoacetate is used for the annelation of aromatic oxo compounds. The method involves condensation with the oxo compound in the presence of TiCl4 followed by rhodium octanoate-catalyzed ring closure to afford fur
