Tetrahedron Letters

Highly stereoselective and efficient synthesis of ω-heterofunctional di-and trienoic esters for Horner–Wadsworth–Emmons reaction via alkyne hydrozirconation and Pd …

G Wang, Z Huang, E Negishi

Index: Wang, Guangwei; Huang, Zhihong; Negishi, Ei-ichi Tetrahedron Letters, 2009 , vol. 50, # 26 p. 3220 - 3223

Full Text: HTML

Citation Number: 17

Abstract

In situ OH metalation with iBu2AlH and hydrozirconation with HZrCp2Cl of HOCH2CCH,(E)- HOCH2CHCHCCH, and HOCH2CCCH3 followed by Pd-catalyzed alkenyl–alkenyl coupling with (E)-BrCHCHCO2Et and (E)-BrCHC (Me) CO2Et using PEPPSI-IPr (7) as a catalyst provides a highly efficient and selective (⩾ 98% all-E) route to ω-hydroxy di-and trienoic acid esters (1a–6a). The corresponding phosphonate esters (1c–4c) of⩾ 98% isomeric purity ...