Key points are not available for this paper at this time.
Herein, a chemodivergent protocol for accessing two distinct chemical spaces from a single starting material is reported. By varying the reaction conditions, O-center enolate and C-center enolate of modified geminal substituted cyclopropane 1,3 keto-esters furnished pyrans and spiro cyclopropanes, respectively. The developed protocol showed a broad functional group tolerance. Mechanistic and theoretical studies indicate that the reaction is initiated by keto group enolization and follows the HSAB principle, leading to distinct products in different media.
Godara et al. (Fri,) studied this question.