Literature DB >> 16615170

A convenient and stereoselective synthesis of (Z)-allyl selenides via Sm/TMSCl system-promoted coupling of Baylis-Hillman adducts with diselenides.

Yun-kui Liu, Dan-qian Xu, Zhen-yuan Xu, Yong-min Zhang.   

Abstract

A simple and convenient procedure for stereoselective synthesis of (Z)-allyl selenides has been developed by a one-pot reaction of diselenides with Baylis-Hillman adducts in the presence of samarium metal-trimethylsilyl chloride under mild conditions. Presumably, the diselenides are cleaved by Sm/TMSCl system to form selenide anions, which then undergo S(N)2' substitution of Baylis-Hillman adducts to produce the (Z)-allyl selenides.

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Year:  2006        PMID: 16615170      PMCID: PMC1462932          DOI: 10.1631/jzus.2006.B0393

Source DB:  PubMed          Journal:  J Zhejiang Univ Sci B        ISSN: 1673-1581            Impact factor:   3.066


  4 in total

1.  Recent advances in the Baylis-Hillman reaction and applications.

Authors:  Deevi Basavaiah; Anumolu Jaganmohan Rao; Tummanapalli Satyanarayana
Journal:  Chem Rev       Date:  2003-03       Impact factor: 60.622

2.  Remarkable activity of a novel cyclic seleninate ester as a glutathione peroxidase mimetic and its facile in situ generation from allyl 3-hydroxypropyl selenide.

Authors:  Thomas G Back; Ziad Moussa
Journal:  J Am Chem Soc       Date:  2002-10-16       Impact factor: 15.419

3.  Pd-catalyzed cross-coupling of Baylis-Hillman acetate adducts with bis(pinacolato)diboron: an efficient route to functionalized allyl borates.

Authors:  George W Kabalka; Bollu Venkataiah; Gang Dong
Journal:  J Org Chem       Date:  2004-08-20       Impact factor: 4.354

4.  Diselenides and allyl selenides as glutathione peroxidase mimetics. Remarkable activity of cyclic seleninates produced in situ by the oxidation of allyl omega-hydroxyalkyl selenides.

Authors:  Thomas G Back; Ziad Moussa
Journal:  J Am Chem Soc       Date:  2003-11-05       Impact factor: 15.419

  4 in total

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