Oxidation of terpenoid diols with chlorine dioxide. Easy preparation of α-hydroxyketones

Фролова, Л. Л.; Попов, А. В.; Bezuglaya, L. V.; Alekseev, I. N.; Слепухин, П. А.; Кучин, А. В.

doi:10.1134/s1070363214050120

Cited by 6 publications

(2 citation statements)

References 12 publications

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“…The recuperated mixture of unreacted trans-diols may eventually be re-oxidized to (+)-2. [116,117] For CrO 3 oxidation of a ketols mixture to camphorquinone (À )-2, see Refs. [94,101,102].…”

Section: Discussionmentioning

confidence: 99%

Regioselective Short Synthesis of Epiisoborneol Neopentyl Ether as Chiral Auxiliary: An Absolute Configuration Reset

Piątek

Chapuis

2021

Helvetica Chimica Acta

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The regio-selective four step synthesis of (1S,2R,3S,4R)-4,7,7-trimethyl-3-(neopentyloxy)bicyclo[2.2.1]heptan-2ol, as recognized efficient chiral auxiliary, is presented. The strategy based on opening of the key acetal 15 (= (2S,3aR,4S,7R,7aS)-2-tert-butyl-4,8,8-trimethylhexahydro-2H-4,7-methano-1,3-benzodioxole) thus circumvents the poor reactivity of the neopentyl electrophile under alkylation conditions. Following the same strategy, but using the unreported acetal 22 (= (2R,3aS,4S,7R,7aR)-2-tert-butyl-4,8,8-trimethylhexahydro-2H-4,7-methano-1,3benzodioxole), the corresponding unreported bis-endo alcohol 23 (= (1R,2R,3S,4S)-3-(2,2-dimethylpropoxy)-4,7,7trimethylbicyclo[2.2.1]heptan-2-ol) could be isolated only in poor yield. An alternative regioselective synthesis, including an ultimate endo-reduction remains to be found. Several erroneous chiroptical properties from the literature are corrected.

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Section: Discussionmentioning

confidence: 99%

Regioselective Short Synthesis of Epiisoborneol Neopentyl Ether as Chiral Auxiliary: An Absolute Configuration Reset

Piątek

Chapuis

2021

Helvetica Chimica Acta

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“…Chlorine dioxide is used for oxidation of alcohols [6,7], sulfur-containing amino acids [8], and thiols and disulfides [9,10], as well as for the preparation of variously structured sulfoxides [11][12][13] and quinones [14][15][16]. There are examples of using chlorine dioxide for oxidation of unsaturated compounds, giving a complex mixture of chlorination products [17,18].…”

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confidence: 99%