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Catalytic Regioselective Isomerization of 2,2‐Disubstituted Oxetanes to Homoallylic Alcohols by Albert Cabré; Sergi Rafael; Giuseppe Sciortino; Gregori Ujaque; Xavier Verdaguer; Agustí Lledós; Antoni Riera is a Chemistry article available to read on EtoBox.
What is Catalytic Regioselective Isomerization of 2,2‐Disubstituted Oxetanes to Homoallylic Alcohols about?
## Abstract The selective isomerization of strained heterocyclic compounds is an important tool in organic synthesis. An unprecedented regioselective isomerization of 2,2‐disubstituted oxetanes into homoallylic alcohols is described. The use of tris(pentafluorophenyl)borane (B(C~6~F~5~)~3~)~,~ a commercially available Lewis acid was key to obtaining good yields and selectivities since other Lewis acids afforded mixtures of isomers and substantial polymerization. The reaction took place under exceptionally mild reaction conditions and very low catalyst loading (0.5 mol %). DFT calculations disclose the mechanistic features of the isomerization and account for the high selectivity displayed by the B(C~6~F~5~)~3~ catalyst. The synthetic applicability of the new reaction is demonstrated by the preparation of γ‐chiral alcohols using iridium‐catalyzed asymmetric hydrogenation.
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- Author
- Albert Cabré; Sergi Rafael; Giuseppe Sciortino; Gregori Ujaque; Xavier Verdaguer; Agustí Lledós; Antoni Riera
- Publisher
- John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Ltd.; Wiley; Research Square (ISSN 0044-8249)
- Published
- 2020
- Language
- EN
- Field
- Chemistry (Physical Sciences)