Lithium diisopropylamide → HCID 86760318, compound

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared from (R)-[but-3-enyl-(1-phenyl-ethyl)-amino]-acetic acid benzyl ester essentially according to the cyclization protocol described in Karoyan, P.; Chassaing, G. Tetrahedron: Asymm. 1997, 8, 2025–2032 with the following modifications: LDA was added at −40° C., then the solution was warmed to 0° C. for 10 min, then re-cooled to −40° C. for the zinc bromide addition. The transmetallation step was omitted and the anion was quenched directly with 2:1 saturated NH4Cl:ammonium hydroxide. Extractive workup (Et2O) afforded an orange oil which was purified by silica gel chromatography (5–10% EtOAc-hexanes) to give the title compound as a yellow oil.

Provenance & Evidence