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. 2016 Jun 16;7(10):6369–6380. doi: 10.1039/c6sc01289b

Scheme 8. Two step synthesis of non-fluorinated VCP-47; activation energies to TS5G value (in blue) were calculated using (U)B3LYP/6-31G* from intermediate 47, gas phase, 298 K, Spartan'10, using conformationally simpler Me ester, units are kcal mol–1). Conditions: (i) ZnEt2 (1 M in hexane, 5 eq.), CH2I2 (10 eq.), 0 °C to r.t., 2.5 h; (ii) TEMPO (0.1 eq.), BAIB (1.1 eq.), DCM, r.t., 3.5 h; (iii) Ph3P Created by potrace 1.16, written by Peter Selinger 2001-2019 C(H)CO2Et (1.3 eq.), 20 h.

Scheme 8