Table 2 Scope study on asymmetric dearomatization of thiophenesa.

From: Organocatalytic enantioselective dearomatization of thiophenes by 1,10-conjugate addition of indole imine methides

  1. aCondition A: 1 (0.20 mmol), 2 (0.24 mmol), (R)-B2 (10 mol%), PhCl (4 mL), −40 oC, 12 h. Condition B: 1 (0.20 mmol), 2 (2 mmol), (R)-B2 (10 mol%), toluene (4 mL), −20 oC, 24 h. Isolated yields. The e.e. values were determined by chiral HPLC.
  2. b30 h.
  3. c−40 oC.
  4. d48 h, yield in parentheses is based on recovered starting material.
  5. e−20 oC, 48 h.
  6. fRun in 0.4-mmol scale.
  7. gRun with 2 equiv of 2, 48 h.
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