Abstract: The generation of metal-containing 1,3-dipoles from metal carbenes represents a significant advance in 1,3-dipolar cycloaddition reactions. However, these transformations have so far been limited to reactions based on diazo compounds or triazoles as precursors. Herein, we disclose a copper-catalyzed enantioselective reaction of alkenyl N-propargyl ynamides with styrene derivatives by formal [3+2] cycloaddition via Cu-containing all-carbon 1,3-dipoles, which constitutes a novel way for the generation of metal-containing 1,3-dipoles via metal carbenes. This protocol allows the practical and atom-economical synthesis of valuable chiral pyrrole-fused bridged [2.2.1] skeletons in moderate to good yields (up to 90% yield) with excellent diastereoselectivities (dr > 50/1) and generally excellent enantioselectivities (up to >99% ee).
Source:https://pcss.xmu.edu.cn/en/info/1095/1889.htm
Full-Link:https://pubs.acs.org/doi/10.1021/jacs.0c01918
