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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 2.

Lithiation-substitution of enantioenriched N-Boc-2-arylpiperidines (see also Figure 1B).

graphic file with name nihms401316u2.jpg
Entry Ar er (R:S) E+ Product % Yield er of product
1 Ph 96:4 MeOD R-3·d1 100a 96:4
2 Ph 96:4 Me2SO4 R-9 79 95:5
3 Ph 96:4 Me3SiCl S-10 88 96:4
4 Ph 96:4 EtOCOCl R-11 85 96:4
5 Ph 96:4 (CD3)2CO R-12 90 95:5
6 Ph 96:4 Allyl-Brb S-13 66 92:8
7 Ph 96:4 BnBrb S-14 71 94:6
8 3,4-(MeO)2-C5H3 97:3 MeOD R-4·d1 100a 97:3
9 3,4-(MeO)2-C6H3 97:3 (CD3)2CO R-15 93 97:3
10 4-(tBu)-C6H4 90:10 MeOD R-5·d1 100a 90:10
11 4-(NC)-C6H4 90:10 MeOD R-6·d1 100a 90:10
12 4-(NC)-C6H4 90:10 Me2SO4 R-16 71 90:10
13 1-Np 97:3 MeOD R-7·d1 100a 97:3
14 1-Np 97:3 Me2SO4 R-17 74 93:7
a

% conversion by GC

b

via zinc and copper-mediated coupling.

b