Table 1. Optimization studies for the divergent cyclopropanation a , b .
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Entry | Base | Solvent | 3a (%) | 4a (%) |
1 | NaH | CH3CN | 13 | — |
2 | NaH | 1,2-DCE | 33 | — |
3 | NaH | DMSO | 19 | 34 |
4 | NaH | DMF | — | 82 c (81 d ) |
5 | NaOMe | DMF | 51 | — |
6 e | NaOMe | DMF | 86 (83 d ) | — |
7 | KOtBu | DMF | 26 | 29 |
aConditions: 1a (0.1 mmol), 2a (2 equiv.), base (2 equiv.), solvent (1 mL), 25 °C, 18 h.
bNMR yield using CH2Br2 as an internal standard.
c2.5 mL of solvent was used.
dIsolated yield.
e2.5 equiv. of 2a and NaH were added to 2.0 mL of solvent at 40 °C.