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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 2.

Nucleophile scope with linchpin 15.[a]

graphic file with name nihms752219u2.jpg
Entry NuLi Product Yield
1 MeLi graphic file with name nihms752219t13.jpg
24
78%
2 graphic file with name nihms752219t14.jpg graphic file with name nihms752219t15.jpg
25
71%
3 graphic file with name nihms752219t16.jpg graphic file with name nihms752219t17.jpg
26
53%
4 graphic file with name nihms752219t18.jpg graphic file with name nihms752219t19.jpg
27
66%
5 graphic file with name nihms752219t20.jpg graphic file with name nihms752219t21.jpg
28
74%
6 graphic file with name nihms752219t22.jpg graphic file with name nihms752219t23.jpg
29
71%
7 graphic file with name nihms752219t24.jpg graphic file with name nihms752219t25.jpg
(R)-30
59%
8 graphic file with name nihms752219t26.jpg graphic file with name nihms752219t27.jpg
(R)-31
68%[b]
9 graphic file with name nihms752219t28.jpg graphic file with name nihms752219t29.jpg
(R)-32
63%[b]
10 graphic file with name nihms752219t30.jpg graphic file with name nihms752219t31.jpg
(R)-33
64%[b]
[a]

Reaction conditions: i) 15, THF, –78° C, then slow addition of NuLi; ii) BnBr, HMPA, THF, –78° C to –30° C; iii) sat. aq. NH4Cl.

[b]

i) 15, THF,–78 ° C, then slow addition of NuLi; ii) BnBr, THF, then slow addition of HMPA/THF solution, –78° C to –30° C; iii) sat. aq. NH4Cl.