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. Author manuscript; available in PMC: 2018 Mar 15.
Published in final edited form as: J Am Chem Soc. 2017 Mar 2;139(10):3647–3650. doi: 10.1021/jacs.7b01124

Table 1.

Alkoxide-directed alkene isomerization.

graphic file with name nihms949311u2.jpg
Entry Variations (& % conversion) 2:14 %2a
1 none (78) 7:1 54
2a 4 equiv. KOt-Bu, no KH (82) 5:1 55
3a 16 equiv. KOt-Bu, no KH (86) 1:1 28
4 1.2 equiv. n-BuLi, no KH (0) – 0
5 DMPU instead of DMSO (0) – 0
Alternate Conditions
6b 20 mol% RhCl3, EtOH/H2O, 70 °C (56) 1:1 28
7a 2 mol% [Co],c 4 mol% PhSiH3, PhH (42) <1:20 <5
a

1H NMR;

b

GCMS;

c

Co(Salt-Bu,t-Bu)Cl•H2O