Fig. 4: Synthesis of chiral benzo-bicyclo[3.2.1]octanes and benzo-tricyclo[6.2.1.04,9]undecenes. | Nature Communications

Fig. 4: Synthesis of chiral benzo-bicyclo[3.2.1]octanes and benzo-tricyclo[6.2.1.04,9]undecenes.

From: Catalytic asymmetric tandem Heck/Sonogashira reaction enabling access to versatile chiral bridged ring scaffolds

Fig. 4

a Synthesis of chiral benzo-bicyclo[3.2.1]octanes. b Synthesis of chiral benzo-tricyclo[6.2.1.04,9]undecenes. aReaction conditions: 13 (0.10 mmol), 2 (0.15 mmol), [(π-allyl)PdCl]2 (5.0 mol%), CuI (12.0 mol%), L2 (20.0 mol%), K2CO3 (3.0 equiv) in 1.0 mL acetone at 70 °C under Ar atmosphere, 20 h. Isolated yields were given. bReaction conditions: 14 (0.10 mmol), Fe(OTf)3 (10.0 mol%) in 1.0 mL DCE at 80 °C under Ar atmosphere, 2 h. c14 (0.10 mmol) in 0.5 mL TFA and 0.5 mL MeCN at 80 °C under Ar atmosphere, 16 h. d3 h. eFe(OTf)3 (20.0 mol%). f14aa (0.10 mmol), ICl (2.0 equiv), NaHCO3 (2.0 equiv) in 1.0 mL MeCN at room temperature under Ar atmosphere, 20 min.

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