Chemical and Stereochemical Aspects of Oxidative Coupling of HPhosphonate and H-Phosphonothioate Diesters. Reactions with N,N-, N,Oand O,O-Binucleophiles

Author(s): Johan Nilsson, Adam Kraszewski, Jacek Stawinski.

Journal Name: Letters in Organic Chemistry

Volume 2 , Issue 2 , 2005

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Abstract:

Efficient protocols for oxidative coupling of dinucleoside H-phosphonate and dinucleoside Hphosphonothioate diesters with 6-aminohexan-1-ol, hexane-1,6-diamine, and hexane-1,6-diol, promoted by iodine were developed. In the instance of coupling with O-nucleophiles, the presence of t-butyldiphenylsilyl chloride and excess of iodine during oxidative coupling were found to have beneficial effect for these reactions in terms of rates and purity of the formed products.

Keywords: h-phosphonates, h-phosphonothioates, binucleophiles, oxidative coupling

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Article Details

VOLUME: 2
ISSUE: 2
Year: 2005
Page: [188 - 197]
Pages: 10
DOI: 10.2174/1570178053202937
Price: $65

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