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Synlett 2019; 30(03): 348-352
DOI: 10.1055/s-0037-1611461
letter
© Georg Thieme Verlag Stuttgart · New York

An Investigation of the Reactions between Azido Alcohols and Phosphoramidites

Jian Wu
a   Department of Chemistry, Case Western Reserve University, 10900 Euclid Avenue, Cleveland, Ohio 44106, USA
,
Lee Bishop
a   Department of Chemistry, Case Western Reserve University, 10900 Euclid Avenue, Cleveland, Ohio 44106, USA
,
Jiatong Guo
b   Department of Chemistry, University of Florida, 214 Leigh Hall, Gainesville, Florida 32611, USA   Email: zguo@chem.ufl.edu
,
Zhongwu Guo*
a   Department of Chemistry, Case Western Reserve University, 10900 Euclid Avenue, Cleveland, Ohio 44106, USA
b   Department of Chemistry, University of Florida, 214 Leigh Hall, Gainesville, Florida 32611, USA   Email: zguo@chem.ufl.edu
› Author AffiliationsOur research work has been supported by NIH/NIGMS (1R01GM090270).
Further Information

Publication History

Received: 09 November 2018

Accepted after revision: 18 December 2018

Publication Date:
16 January 2019 (online)

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Abstract

The reactions of several β-, γ-, and δ-azido alcohols with dibenzyl and dimethyl N,N-diisopropylphosphoramidites were examined. Detailed analysis of the intermediates and products formed from the reactions under different conditions provided useful information to gain insights into their mechanisms involving intramolecular Staudinger reaction, as well as the structure–reactivity relationships of both substrates. The reactions of γ- and δ-azido alcohols with dibenzyl N,N-diisopropylphosphoramidite could produce 6- and 7-membered cyclic phosphoramidates, thereby providing a new synthetic method for these biologically important molecules.

Key words

Staudinger reaction - azido alcohol - phosphoramidite - ­cyclic phosphoramidate - cyclization

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611461.
  • Supporting Information
 

  • References and Notes


      • New addresses:
    • 1a Wu J., Progenra, Inc., 277 Great Valley Parkway, Malvern, PA 19355 USA.
    • 1b L. Bishop, Lawrence Hall of ­Science, University of California, Berkeley, CA 94720, USA.
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