69618-26-4Relevant academic research and scientific papers
Synthesis and Isolation of Organogold Complexes through a Controlled 1,2-Silyl Migration
McGee, Philippe,Bellavance, Gabriel,Korobkov, Ilia,Tarasewicz, Anika,Barriault, Louis
supporting information, p. 9662 - 9665 (2015/06/30)
During our efforts toward the synthesis of naturally occurring polyprenylated polycyclic acylphloroglucinol using a AuI-catalyzed 6-endo dig carbocyclization, we isolated stable vinyllic gold intermediates. Optimization lead to isolated yields of up to 98 %, using 2-(di-tert-butylphosphino)biphenyl as the ligand. This transformation is derived from a silyl rearrangement that can be fully controlled according to the nature of the substituent on the ynone. This selective transformation does not require basic conditions to prevent protodeauration. These vinylgold complexes are the first isolated intermediates during a silyl migration with gold(I). More than 16 new organogold complexes were synthesized and characterized by single-crystal X-ray diffraction. Reactivity of these complexes is also presented.
Stereoselective synthesis of complex polycyclic aziridines: Use of the Bronsted acid-catalyzed aza-Darzens reaction to prepare an orthogonally protected mitomycin C intermediate with maximal convergency
Srinivasan, Jayasree M.,Mathew, Priya A.,Williams, Amie L.,Huffman, John C.,Johnston, Jeffrey N.
scheme or table, p. 3975 - 3977 (2011/05/04)
A concise synthesis of a highly functionalized intermediate lacking only C10 of the mitomycin backbone is described. The key to this development is the Bronsted acid-catalyzed aza-Darzens reaction used to forge the cis-aziridine. Additionally an oxidative
Selective oxidation of propargylic alcohols into α,β-acetylenic aldehydes with a TiCl4/Et3N system
Han,Shinokubo,Oshima
, p. 1421 - 1422 (2007/10/03)
A TiCl4/Et3N combination proved to be effective for the selective oxidation of propargylic alcohols into α,β-acetylenic aldehydes in good yields. Treatment of 2-hexyne-1,6-diol with TiCl4/Et3N provided 6-hydroxy-2-hexynal in good yield.
