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Lithium, reaction with 2,6-dimethylphenol

Asymmetric Buchner reactions using chiral auxiliary have also been undertaken. The diazoketo substrate 126 for the chiral tethered Buchner reaction is prepared from optically pure (2/ ,4/f)-2,4-pentanediol in three steps the Mitsunobu reaction with 3,5-dimethylphenol, esterification with diketene, and diazo formation/deacetylation. Treatment of 126 with rhodium(II) acetate results in a quantitative yield of 127 with more than 99% ee. This compound is reduced with lithium aluminium hydride, and the resulting diol 128 undergoes epoxidation and concurrent acetal formation to give 129 as a single diastereomer. Hydrogenation of 129 with Raney nickel proceeds stereoselectively to yield saturated diol 130, which is converted to aldehyde 132 via acid hydrolysis followed by oxidation. Compound 132 is a versatile intermediate for natural product synthesis. [Pg.442]


See other pages where Lithium, reaction with 2,6-dimethylphenol is mentioned: [Pg.370]    [Pg.142]    [Pg.8]   
See also in sourсe #XX -- [ Pg.46 , Pg.115 ]

See also in sourсe #XX -- [ Pg.46 , Pg.115 ]

See also in sourсe #XX -- [ Pg.46 , Pg.115 ]




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2.6- Dimethylphenol, reaction with

Dimethylphenol

Dimethylphenol reactions

Dimethylphenols

Reaction with lithium

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