Asymmeric Formal [3+3]-Cycloaddition Reactions of Nitrones with Electrophilic Vinylcarbene Intermediates

作者:Wang Xiaochen; Xu Xinfang; Zavalij Peter Y; Doyle Michael P*
来源:Journal of the American Chemical Society, 2011, 133(41): 16402-16405.
DOI:10.1021/ja207664r

摘要

With metal carbene access to dipolar intermediates, 3,6-dihydro-1,2-oxazines are produced in high yields by dirhodium(II) carboxylate catalyzed reactions between nitrones and a beta-TBSO-substituted vinyldiazoacetate. High enantiocontrol occurs with catalysis by N-phthaloyl-(S)-(amino acid)-ligated dirhodium carboxylates for [3 + 3]-cycloaddition reactions with both acyclic and cyclic nitrones.

  • 出版日期2011-10-19