689294-94-8Relevant academic research and scientific papers
Multicomponent reactions of diazoamides: Diastereoselective synthesis of mono- and bis-spirofurooxindoles
Muthusamy, Sengodagounder,Gunanathan, Chidambaram,Nethaji, Munirathinam
, p. 5631 - 5637 (2004)
This paper describes the intermolecular generation of carbonyl ylides by dirhodium(II) tetraacetatecatalyzed reaction of 3-diazoindol-2-ones in the presence of aryl aldehydes and heteroaryl aldehydes. These carbonyl ylides were subsequently trapped with dipolarophiles such as dimethyl acetylene- dicarboxylate, maleic anhydride, and ethyl acrylate to afford spirofurooxindoles. Consequently, diastereoselective synthesis of spirodihydrofurooxindoles through the multicomponent reactions of cyclic diazoamides was successfully achieved for the first time. The stereochemistry of the spirofurooxindole is unequivocally corroborated by the single-crystal X-ray analysis of the representative product 4o. Interestingly, these reactions were extended to double multicomponent reactions of bis-cyclic diazoamides to afford the respective complex polycycles in a tandem manner, which led to the construction of four carbon-carbon bonds, two carbon-oxygen bonds, and four chiral centers in a single synthetic step.
Stereoselective epoxide generation with cyclic rhodium carbenoids: A new access to spiro-indolooxiranes
Muthusamy, Sengodagounder,Gunanathan, Chidambaram,Nethaji, Munirathinam
, p. 639 - 642 (2007/10/03)
The reaction of cyclic diazoamides with aryl aldehydes catalyzed by rhodium(II) acetate leads to intermolecular stereoselective epoxide ring formation. A series of spiro-indolooxiranes has been synthesized following the described method in a facile manner. The use of aryl dialdehydes in the course of reaction of cyclic diazoamide resulted the formation of bis-spiro- indolooxiranes.
