Fig. 4: Gram-scale reaction, further transformation and application of chiral bridged bicyclo[3.3.1]nonane. | Nature Communications

Fig. 4: Gram-scale reaction, further transformation and application of chiral bridged bicyclo[3.3.1]nonane.

From: Switchable organocatalytic enantioselective sulfenocyclization of cyclohexadienes enabling chemodivergent access to chiral bicyclo[m.n.1] ring systems

Fig. 4

a Gram-scale reactions. b Further transformation of chiral bridged bicyclo[3.3.1]nonane. Reaction conditions: a) H2O2 (1.8 equiv.), HFIP, 25 oC, 18 h, 62%, 4:1 dr, 94% ee. b) m-CPBA (6.0 equiv.), CH2Cl2, 42%, 94% ee. c) m-CPBA (2.5 equiv.), CH2Cl2, 60%, 94% ee. d) Mg, MeOH, 25 oC, 24 h, 99%, 94% ee. e) (i) n-BuLi (1.2 equiv.), Et2O (0.1 M), 0 oC; (ii) ICH2Cl (3.0 equiv.), i-PrMgCl (3.0 equiv.), THF, −78 oC, 45 min then −60 oC, 12 h. 25% for two steps, 96% ee. c Evaluation of 4’ as potential ligand in asymmetric catalysis.

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