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. Author manuscript; available in PMC: 2013 Sep 12.
Published in final edited form as: J Am Chem Soc. 2012 Aug 27;134(36):14764–14771. doi: 10.1021/ja306276w

Table 1.

Evaluating the configurational stability of N-Boc-2-lithio-2-phenylpiperidine 8.

graphic file with name nihms401316u1.jpg
Entry Solvent Ligand er of 3·d1 (R:S)
1 Et2O 1 equiv TMEDA 96:4
2 Et2O 4 equiv TMEDA 96:4
3a Et2O 4 equiv TMEDA 85:15
4 Et2O Noneb 91:9
5 THF 1 equiv TMEDA 94:6
6 THF 4 equiv TMEDA 95:5
7 THF Noneb 92:8
a

transferred to a bath at −55 °C and stirred for 1 h,

b

lithiated for 1 h