Fig. 6: Gram-scale reaction and synthetic applications. | Nature Communications

Fig. 6: Gram-scale reaction and synthetic applications.

From: Enantioselective synthesis of inherently chiral sulfur-containing calix[4]arenes via chiral sulfide catalyzed desymmetrizing aromatic sulfenylation

Fig. 6: Gram-scale reaction and synthetic applications.

a The reaction was conducted with 2a (1.43 mmol, 1.0 equiv), 3a (1.72 mmol, 1.2 equiv), (S, R)-1g (0.143 mmol, 0.1 equiv), pTSA (0.143 mmol, 0.1 equiv), HFIP (2.86 mmol, 2.0 equiv), and 3 Å MS (572 mg) in DCM (28.6 mL) at −10 °C under Ar for 22 h. b The reaction was conducted with 4a (0.1 mmol, 1.0 equiv), mCPBA (0.1 mmol, 1.0 equiv), and NaHCO3 (0.5 mmol, 5.0 equiv) in DCM (2 mL) at −20 °C under Ar for 24 h. c The reaction was conducted with 4a (0.1 mmol, 1.0 equiv) and mCPBA (0.3 mmol, 3.0 equiv) in DCM (2 mL) at rt under Ar for 7 h. d The reaction was conducted with 4ac (0.012 mmol, 1.0 equiv) and DDQ (0.024 mmol, 2.0 equiv) in DCM (0.5 mL) and H2O (0.1 mL) at 0 °C under Ar for 1.5 h. pTSA p-toluenesulfonic acid, HFIP hexafluoroisopropanol, mCPBA = 3-chloroperoxybenzoic acid, DDQ = 2,3-dichloro-5,6-dicyano−1,4-benzoquinone.

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