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Gold(I)‐Catalyzed Tandem Reaction of γ ‐Amino‐Substituted Propargylic Esters to Pyrrolines and its Application in the Formal Synthesis of (±)‐Aphanorphine
Author(s) -
Wang Zhengshen,
Zheng Huaiji,
Yang Juan,
Xie Xingang,
She Xuegong
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201401161
Subject(s) - chemistry , tandem , catalysis , intramolecular force , combinatorial chemistry , formal synthesis , reaction conditions , amino esters , tosyl , cascade reaction , pyrroline , organic chemistry , medicinal chemistry , materials science , composite material
An effective synthesis of structurally diverse pyrroline derivatives has been accomplished by a gold(I)‐catalyzed tandem 1,3‐acyloxy rearrangement/intramolecular azacylization reaction of γ ‐amino‐substituted propargylic esters in good to excellent chemical yields (52–98%). The reaction proceeds under extremely mild conditions and has also demonstrated its potential in a concise formal synthesis of (±)‐aphanorphine with a catalyst loading as low as 0.5 mol% to provide the key intermediate 5‐(4‐methoxybenzyl)‐1‐tosyl‐2,5‐dihydro‐1 H ‐pyrrol‐3‐yl pivalate on a gram scale.