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. Author manuscript; available in PMC: 2008 Oct 26.
Published in final edited form as: J Org Chem. 2007 Oct 2;72(22):8506–8518. doi: 10.1021/jo7013559

Table 1.

Conversion of 15 to enol triflate 14.a

entry base Time Yield E:Z
1 KHMDS 15 h 63% 25:75
2 NaHMDS 15 h 61% 40:60
3 LiHMDS 7 d 28% >95:5
4 NaH 15 h 72% 54:46
5 MesLi 4 d 20% >95:5
6 LiH 7 d 65% 93:7
a

Enolate generated in THF at −78 °C, N-phenylbistriflimide added and warmed to and stirred (time: see table).