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. Author manuscript; available in PMC: 2017 Jan 4.
Published in final edited form as: Angew Chem Int Ed Engl. 2015 Nov 20;55(1):232–235. doi: 10.1002/anie.201509342

Table 3.

Preparation of cyclic systems utilizing 15.[a]

graphic file with name nihms752219u3.jpg
Entry NuLi E+ Quench Product Yield
1 nBuLi graphic file with name nihms752219t32.jpg A graphic file with name nihms752219t33.jpg
41
68%
2 nBuLi graphic file with name nihms752219t34.jpg A graphic file with name nihms752219t35.jpg
42
69%
3 nBuLi graphic file with name nihms752219t34.jpg B graphic file with name nihms752219t36.jpg
43
72%
4 graphic file with name nihms752219t37.jpg
44
BnBr B graphic file with name nihms752219t38.jpg
45
60%
5 graphic file with name nihms752219t37.jpg
44
graphic file with name nihms752219t32.jpg B graphic file with name nihms752219t39.jpg 64%
6 graphic file with name nihms752219t40.jpg
47
graphic file with name nihms752219t34.jpg B graphic file with name nihms752219t41.jpg 67%
[a]

Reaction conditions: i) 15, Et2O, –78 ° C, then slow addition of NuLi; ii) BnBr, HMPA, Et2O, –78 ° C to –30° C; iii) quench A with sat. aq. NH4Cl or quench B with 48 % aq. HF, then NaHCO3.