Extended Data Table 1 Reaction optimization
- aGeneral oxidation (unless otherwise noted): 2 (0.3 mmol), catalyst (x mol%, (R,R) and (S,S) enantiomers used interchangeably), AcOH (15 equiv.), MeCN (0.5 M), −36 °C; H2O2 (2 equiv.) in MeCN (3.75 ml) syringe pump 1 h. Mixture passed through silica plug, EtOAc flush, concentrated before isolation or methylation. Isolated yields are based on the average of three experiments, unless otherwise noted. bProcedure from ref. 28. cProcedure from ref. 29. dProcedure from ref. 31. e5 equiv. H2O2. fGeneral BF3 alkylation: crude in CH2Cl2 (0.2 M), −78 °C, AlMe3 (3 equiv.) and BF3•OEt2 (2 equiv.) sequentially added, stirred 1 h; room temperature (rt) for 3 h. gGeneral fluorine alkylation: crude in CH2Cl2 (0.2 M), fluorine additive (1 equiv.) added at −78 °C; rt for 1 h; cooled to −78 °C, nucleophile (3 equiv.) added, stirred 2 h; rt for 1 h. hGeneral TMSOTf alkylation: crude in CH2Cl2 (0.2 M), TFAA (1 equiv.) added, stirred 1 h; cooled to −78 °C, AlMe3 (3 equiv.) and TMSOTf (1 equiv.) sequentially added, stirred 2 h; rt for 1 h. iCrude in CH2Cl2 (0.2 M), MsCl (1 equiv.) and Et3N (1 equiv.) added, stirred 1 h; washed NaHCO3, dried, reduced; redissolved in CH2Cl2, AlMe3 (3 equiv.) added at −78 °C, stirred 2 h; rt for 1 h. jMeMgBr (3 equiv.) added at −78 °C, stirred 3 h. kYield determined by crude 1H-NMR.
