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

Teruaki Mukaiyama; Kiichi Kuroda; Yuji Maruyama; Yujiro Hayashi

doi:10.1246/cl.2008.1072

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

Teruaki Mukaiyama, Kiichi Kuroda, Yuji Maruyama, Yujiro Hayashi

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	1072-1073
Number of pages	2
Journal	Chemistry Letters
Volume	37
Issue number	10
DOIs	https://doi.org/10.1246/cl.2008.1072
Publication status	Published - 2008
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)

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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. / Mukaiyama, Teruaki; Kuroda, Kiichi; Maruyama, Yuji; Hayashi, Yujiro.

In: Chemistry Letters, Vol. 37, No. 10, 2008, p. 1072-1073.

Research output: Contribution to journal › Article › peer-review

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abstract = "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.",

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AU - Kuroda, Kiichi

AU - Maruyama, Yuji

AU - Hayashi, Yujiro

PY - 2008

Y1 - 2008

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AB - 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.

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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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