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. Author manuscript; available in PMC: 2014 Sep 20.
Published in final edited form as: J Org Chem. 2013 Sep 5;78(18):10.1021/jo4013964. doi: 10.1021/jo4013964

Table 1.

The intramolecular Friedel-Crafts alkylation of 25

graphic file with name nihms522414t1.jpg
entry conditions T (°C) time product % yield (ee)
1 HCO2H, H3PO4 115 12 h 26+28 18 + 38
2 HCO2H, 31c 110 96 h 26+28 43 + 14
3 BBr3, CH2Cl2 −78 to 0 30 min 27 45
4 BF3·Et2O, CH2Cl2 −78 to rt 2h 27 0
5 TMSI, toluene 70 4h 30 54
6 32, BBr3, CH2Cl2 0 20 min 27 20 (< 20)