Ethyl 1,3-dithiolane-2-carboxylate

Chemical properties

clear light yellow liquid

General Description

Ethyl 1,3-dithiolane-2-carboxylate is an α-keto acid equivalent. It participates in the conjugate additions to enones. It is a bulky equivalent of acetate undergoing syn-selective aldol reactions. Anion derived from ethyl 1,3-dithiolane-2-carboxylate participates as nucleophile during the total synthesis of the corynanthe alkaloid dihydrocorynantheol and the formal syntheses of the indole alkaloids tacamonine, rhynchophylline and hirsutine. It also participates in the conjugate addition of enolates to phenylglycinol-derived α,β-unsaturated δ-lactams.

Purification Methods

Dissolve the ester in CHCl3, wash it with aqueous K2CO3, twice with H2O, dry it over MgSO4, filter, evaporate and distil the residue in vacuo. [Hermann et al Tetrahedron Lett 2599 1973, Corey & Erickson J Org Chem 36 3553 1971]. [Beilstein 19/7 V 225.]