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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 1.

Electrophile scope with linchpin 15.[a]

graphic file with name nihms752219u1.jpg
Entry E+ Product Yield
1 Mel graphic file with name nihms752219t1.jpg
17
78%
2 graphic file with name nihms752219t2.jpg graphic file with name nihms752219t3.jpg
18
75%
3 graphic file with name nihms752219t4.jpg
a)X=Br
b)X=1
graphic file with name nihms752219t5.jpg
19
a) 59%
b) 74%
4 graphic file with name nihms752219t6.jpg
a)X=Br
b)X=1
graphic file with name nihms752219t7.jpg
20
a) 52%
b) 67%
5 graphic file with name nihms752219t8.jpg
a)X=Br
b)X=1
graphic file with name nihms752219t9.jpg
21
a) 55%
b) 69%
6 Et3SiCl graphic file with name nihms752219t10.jpg
22
71%
7 graphic file with name nihms752219t11.jpg
(R)-epichiorohydrin
graphic file with name nihms752219t12.jpg
(R)-23
60%
[a]

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