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Stereoselective Synthesis of ( E )‐ and ( Z )‐Allylphosphonium Salts by Palladium‐Catalyzed Addition of Phosphine to Allene
Author(s) -
Arisawa Mieko,
Yamaguchi Masahiko
Publication year - 2001
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 - 10.1002/1615-4169(20010129)343:1<27::aid-adsc27>3.0.co;2-u
Subject(s) - chemistry , allene , methanesulfonic acid , phosphine , palladium , salt (chemistry) , stereoselectivity , catalysis , wittig reaction , medicinal chemistry , organic chemistry
The palladium‐catalyzed addition of phosphine to allene in the presence of methanesulfonic acid stereoselectively gives the ( E )‐ or ( Z )‐allylphosphonium salt. The ( E )‐allylphosphonium salt is formed by performing the reaction in THF under reflux and the ( Z )‐allylphosphonium salt is obtained at –10 °C. The ( E )‐ and ( Z )‐allylphosphonium salts are used in the Wittig olefination reaction, and their diastereoselectivities are compared.