Sodium Iodide/ tert ‐Butyl(dimethyl)silyl Chloride‐Induced Isomerization of 2,3‐Allenols to 2( E )‐Enals | Zendy

Zeng Rong | Zendy; Ma Zhichao | Zendy; Fu Chunling | Zendy; Ma Shengming | Zendy

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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.

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