A New Synthesis of cis-Diol from Alkene Using Iodine-Ammonium Cerium(IV) Nitrate

C. Akira Horiuchi; Gong Dan; Masaki Sakamoto; Kazuhiko Suda; Shigeru Usui; Okihiko Sakamoto; Shinya Kitoh; Satoshi Watanabe; Takamitsu Utsukihara; Sukekatsu Nozaki

doi:10.1055/s-2005-916040

PAPER

A New Synthesis of cis-Diol from Alkene Using Iodine-Ammonium Cerium(IV) Nitrate

C. Akira Horiuchi*^a, Gong Dan^a, Masaki Sakamoto^a, Kazuhiko Suda^a, Shigeru Usui^a, Okihiko Sakamoto^a, Shinya Kitoh^a, Satoshi Watanabe^a, Takamitsu Utsukihara^a, Sukekatsu Nozaki^b
^a Department of Chemistry, Rikkyo (St. Paul’s) University, Nishi-Ikebukuro, Toshima-Ku, Tokyo 171-8501, Japan
Fax: +81(3)39852397; e-Mail: horiuchi@rikkyo.ac.jp; e-Mail: cahoriuchi@nifty.com;
^b Faculty of Pharmaceutical Science, Josai University, Sakado, Saitama 350-0295, Japan

Abstract

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Abstract

The reaction mixtures of 5α-cholest-2-ene with iodine-ammonium cerium(IV) nitrate [CAN(IV)] were converted with potassium hydroxide in methanol-water to give the more hindered 2β,3β-diol in high yield. Cyclohexene and cycloheptene similarly reacted to the corresponding cis-diols in good yield. It was found that this reaction intermediate proceeds to give trans-iodoacetate via trans-iodonitrate. This new synthetic method provided several advantages over the Prevost reaction.

Key words

iodine-ammonium cerium(IV) nitrate - cis-diols - trans-iodoacetate - trans-iodonitrate

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References

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