Get access

Palladium-Catalyzed Three-Component Cascade Cyclization Reaction of Bisallenes with Propargylic Carbonates and Organoboronic Acids: Efficient Construction of cis-Fused Bicyclo[4.3.0]nonenes

Authors

  • Wei Shu,

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 (P.R. China), Fax: (+86) 21-6416-7510
    Search for more papers by this author
  • Guochen Jia Prof. Dr.,

    1. Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong (P.R. China)
    Search for more papers by this author
  • Shengming Ma Prof. Dr.

    1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 (P.R. China), Fax: (+86) 21-6416-7510
    Search for more papers by this author

  • Financial support from the National Natural Science Foundation of China (20429201 and 20732005), the State Basic and Research Development Program (Grant No. 2006CB806105), and the Chinese Academy of Sciences is greatly appreciated. We also thank Xiongdong Lian for reproducing the results of entries 1, 2, and 8 in Table 2.

Abstract

Aus 3 mach 1: Die Titelreaktion liefert cis-anellierte Bicyclo[4.3.0]nonene aus leicht verfügbaren 1,5-Bisallenen sowie strukturell unterschiedlichen Propargylcarbonaten und Arylboronsäuren (siehe Schema; X=NTs, C(E1)2 mit E1=CO2Bn, SO2Ph; dba=trans,trans-Dibenzylidenaceton). Der postulierte Mechanismus umfasst eine sequenzielle oxidative Addition, drei Carbopalladierungen in zwei unterschiedlichen Varianten sowie eine Suzuki-Kupplung.

original image

Ancillary