A Direct Approach to Enantiopure Propionate Derivatives from Ethyl Lactate

David Clemente-Tejeda (1) , Juan A. Lara (1) , Samir Z. Zard (1)

1 DCSO - Laboratoire de synthèse organique

The S-propargyl xanthate derived from ethyl (S)-lactate reacts upon heating with various acidic substances to give the propionate transfer product in high yield and with complete inversion of configuration.

Keywords: S-propargyl xanthate; sigmatropic rearrangement; esters; inversion; propionates

Domains: Chemical Sciences; Organic chemistry

David Clemente-Tejeda, Juan A. Lara, Samir Z. Zard. A Direct Approach to Enantiopure Propionate Derivatives from Ethyl Lactate. Synthesis: Journal of Synthetic Organic Chemistry, 2016, 48 (19), pp.3393-3399. ⟨10.1055/s-0035-1562449⟩. ⟨hal-02096722⟩