- A new type of oxidation-reduction condensation by the combined use of phenyl diphenylphosphinite and oxidant
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A new type of oxidation-reduction condensation of alcohols with sulfur, nitrogen, and oxygen nucleophiles by the combined use of phenyl diphenylphosphinite (PhOPPh2) and oxidants such as azides or diethyl azodicarboxylate (DEAD) are described. In these reactions, chiral secondary and tertiary alcohols are converted into the corresponding chiral sulfides, azides, esters and ethers under mild and neutral conditions with almost complete inversion of stereochemical configuration.
- Mukaiyama, Teruaki,Kuroda, Kiichi,Maruyama, Yuji
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scheme or table
p. 63 - 82
(2010/04/23)
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- Mitsunobu approach to the synthesis of optically active α,α-disubstituted amino acids
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Chiral tertiary α-hydroxy esters of known stereochemical configuration were transformed to α-azido esters by Mitsunobu reaction with HN3. Optimization of this reaction was shown to proceed at room temperature with high chemical yield using 1,1-(azodicarbonyl)dipiperidine (ADDP) and trimethylphosphine (PMe3). Complete inversion of configuration was observed at the α-carbon. Several α,α- disubstituted amino acids were synthesized in high overall chemical yield and optical purity.
- Green, Jonathan E.,Bender, David M.,Jackson, Stona,O'donnell, Martin J.,Mccarthy, James R.
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supporting information; experimental part
p. 807 - 810
(2009/08/08)
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- Stereospecific synthesis of sec- and tert-alkyl azides from alcohols and trimethylsilyl azide by a new type of oxidation-reduction condensation using phenyl diphenylphosphinite and trimethylsilylmethyl azide
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A novel method for the preparation of alkyl azides from alcohols and trimethylsilyl azide by a new type of oxidation-reduction condensation using phenyl diphenylphosphinite and trimethylsilylmethyl azide is described. Chiral secondary and tertiary alcohols are converted into the corresponding chiral azides with almost complete inversion of configuration under mild and neutral conditions. Copyright
- Mukaiyama, Teruaki,Kuroda, Kiichi,Maruyama, Yuji,Hayashi, Yujiro
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scheme or table
p. 1072 - 1073
(2009/12/02)
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