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. Author manuscript; available in PMC: 2014 Nov 6.
Published in final edited form as: J Am Chem Soc. 2013 Nov 6;135(44):16720–16735. doi: 10.1021/ja409013m

Table 8.

One-step functionalization of the exocyclic olefin.

graphic file with name nihms529400t8.jpg
Entry Conditions Product Result
1 LDA (1 equiv.), THF, −78 °C, then NaHSO4 78a (X=H) >90% conv., 18% yield
2 LDA (2 equiv.), THF, 23 °C, then NaHSO4 78a >90% conv., 18% yield
3 KHMDS (2.0 equiv.), THF, 23 °C, then NaHSO4 78a 100% conv., <36% yield
4 KOt-Bu (2 equiv.), THF, 23 °C, then NaHSO4 78a 100% conv., 58% yield
5 KOt-Bu (2 equiv.), THF, 23 °C, then Br2 78b (X=Br) 100% conv, 0% yield
6 LiOt-Bu (1 equiv.), n-BuLi (1.5 equiv.), then CD3CO2D 78c (X=D) 85% yield
7 LiOt-Bu (1 equiv.), n-BuLi (1.5 equiv.), then (BzO)2 78d (X=OBn) decomp.
8 LiOt-Bu (1 equiv.), n-BuLi (1.5 equiv.), then DMDO 78e (X=OH) trace product
9 LiOt-Bu (1 equiv.), n-BuLi (1.5 equiv.), then 79 78e 64% yield
10 HOt-Bu (0.5 equiv.), then n-BuLi (1.1 equiv.), then 79 78e 0% yield