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Sodium Iodide/ tert ‐Butyl(dimethyl)silyl Chloride‐Induced Isomerization of 2,3‐Allenols to 2( E )‐Enals
Author(s) -
Zeng Rong,
Ma Zhichao,
Fu Chunling,
Ma Shengming
Publication year - 2014
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.201300835
Subject(s) - chemistry , isomerization , sodium iodide , substituent , silylation , iodide , methyl iodide , medicinal chemistry , deuterium , sodium , chloride , iodine , polar effect , organic chemistry , catalysis , physics , quantum mechanics
Through an unexpected CC bond migration, 2( E )‐enals were efficiently prepared highly stereoselectively in moderate to good yields via the sodium iodide/ tert ‐butyl(dimethyl)silyl chloride (NaI/TBSCl)‐mediated reaction of the easily available 2,3‐allenols. Based on a careful mechanistic study, including control experiments and deuterium‐labeling experiments, an electron‐withdrawing substituent group in the 4 position has been proven to be crucial and a possible mechanism has been proposed.