Phosphine-Mediated Multi-Component γ-Umpolung/Aldol/Wittig Cascade Reaction for the Synthesis of Functionalized Naphthalenes

by Kui Zhang

Institution: UCLA
Department: Chemistry
Year: 2013
Keywords: Chemistry; γ-umpolung; multi-component reaction; naphthalene; phosphine-mediated; Wittig reaction
Record ID: 2020152
Full text PDF: http://www.escholarship.org/uc/item/77m3r61j


This study describes an efficient and convenient triphenylphosphine-mediated γ-umpolung/aldol/Wittig cascade reaction. This is the first time that phosphine has been used to mediate a multi-component coupling reaction involving alleonates, nucleophiles, and substituted o-phthalaldehyde to synthesize naphthalenes. The reaction condition has been optimized and employed in the synthesis of eight functionalized naphthalenes. This reaction proceeds under mild conditions and produces good to excellent yields.