Literature DB >> 16604566

The efficient direct synthesis of N,O-acetal compounds as key intermediates of discorhabdin A: oxidative fragmentation reaction of alpha-amino acids or beta-amino alcohols by using hypervalent iodine(III) reagents.

Yu Harayama1, Masako Yoshida, Daigo Kamimura, Yasufumi Wada, Yasuyuki Kita.   

Abstract

Hypervalent iodine(III) reagents are readily available, easy to handle, and have a low toxicity and similar reactivities to those of heavy metal reagents, and hence they are used for various oxidative reactions. The oxidative cleavage of alkynes or carbonyl compounds by using bis(trifluoroacetoxy)iodo(III) pentafluorobenzene (C(6)F(5)I(OCOCF(3))(2)) has been reported. Herein, the efficient direct synthesis of N,O-acetal compounds as key intermediates of discorhabdin A, by the oxidative fragmentation reaction of alpha-amino acids or beta-amino alcohols by using C(6)F(5)I(OCOCF(3))(2), is described.

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Year:  2006        PMID: 16604566     DOI: 10.1002/chem.200501635

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  4 in total

Review 1.  Chemistry of polyvalent iodine.

Authors:  Viktor V Zhdankin; Peter J Stang
Journal:  Chem Rev       Date:  2008-12       Impact factor: 60.622

2.  Enantioselective Synthesis of Indolines, Benzodihydrothiophenes, and Indanes by C-H Insertion of Donor/Donor Carbenes.

Authors:  Lucas W Souza; Richard A Squitieri; Christine A Dimirjian; Blanka M Hodur; Leslie A Nickerson; Corinne N Penrod; Jesus Cordova; James C Fettinger; Jared T Shaw
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-18       Impact factor: 15.336

Review 3.  Synthesis of the marine pyrroloiminoquinone alkaloids, discorhabdins.

Authors:  Yasufumi Wada; Hiromichi Fujioka; Yasuyuki Kita
Journal:  Mar Drugs       Date:  2010-04-21       Impact factor: 5.118

Review 4.  Recent Synthetic Applications of the Hypervalent Iodine(III) Reagents in Visible-Light-Induced Photoredox Catalysis.

Authors:  Chaoyue Chen; Xin Wang; Tinghai Yang
Journal:  Front Chem       Date:  2020-09-23       Impact factor: 5.221

  4 in total

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