Acid-catalyzed [4+3] cycloaddition reaction of N-nosyl pyrroles

作者：Shibata Miki; Fuchigami Ryuichi; Kotaka Ryota; Namba Kosuke^*; Tanino Keiji

来源：Tetrahedron, 2015, 71(26-27): 4495-4499.

DOI：10.1016/j.tet.2015.02.071

• Tropane alkaloid
• Tropinone
• [4+3] Cycloaddition reaction
• N-Nosyl pyrroles

An acid-catalyzed [4+3] cycloaddition reaction of N-nosyl pyrroles with 2-(tert-butyldimethylsilyloxy) acrolein has been developed. The reaction of 2-(silyloxy)acrolein with N-nosyl pyrrole was catalyzed by Tf2NH, and a regio- and stereoselective reaction with 2-substituted N-nosyl pyrroles leading to tropinone derivatives possessing tetra-substituted carbon centers was also achieved. High regioselectivities were obtained by using Cu(OTf)(2) or Sc(OTf)(3) as a catalyst in nitromethane, and the reaction was applicable to various 2-substituted N-nosyl pyrroles in good yields and with high regioselectivities.

• 出版日期2015-7-1