Synthesis and Characterization of Privileged Monodentate Phosphoramidite Ligands and Chiral Brønsted Acids Derived from D-Mannitol

doi:10.3390/ijms13032727

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Int. J. Mol. Sci. 2012, 13(3), 2727-2743; doi:10.3390/ijms13032727

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Synthesis and Characterization of Privileged Monodentate Phosphoramidite Ligands and Chiral Brønsted Acids Derived from D-Mannitol

Abdullah Mohammed A. Al-Majid* , Assem Barakat* , Yahia Nasser Mabkhot and Mohammad Shahidul Islam

Department of Chemistry, Faculty of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia

* Authors to whom correspondence should be addressed.

Received: 28 December 2011; in revised form: 6 February 2012 / Accepted: 20 February 2012 / Published: 29 February 2012

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Abstract: The synthesis of several novel chiral phosphoramidite ligands (L1–L8) with C₂ symmetric, pseudo C₂ symmetric secondary amines and chiral Brønsted acids 1a,b has been achieved. These chiral auxiliaries were obtained from commercially available d-mannitol, and secondary amines in moderate to excellent yields. Excellent diastereoselectivites of ten chiral auxiliaries were obtained. The chiral phosphoramidite ligands and chiral Brønsted acids were fully characterized by spectroscopic methods.

Keywords: phosphoramidite; Brønsted acid; d-mannitol

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MDPI and ACS Style

Al-Majid, A.M.A.; Barakat, A.; Mabkhot, Y.N.; Islam, M.S. Synthesis and Characterization of Privileged Monodentate Phosphoramidite Ligands and Chiral Brønsted Acids Derived from D-Mannitol. Int. J. Mol. Sci. 2012, 13, 2727-2743.

AMA Style

Al-Majid AMA, Barakat A, Mabkhot YN, Islam MS. Synthesis and Characterization of Privileged Monodentate Phosphoramidite Ligands and Chiral Brønsted Acids Derived from D-Mannitol. International Journal of Molecular Sciences. 2012; 13(3):2727-2743.

Chicago/Turabian Style

Al-Majid, Abdullah Mohammed A.; Barakat, Assem; Mabkhot, Yahia Nasser; Islam, Mohammad Shahidul. 2012. "Synthesis and Characterization of Privileged Monodentate Phosphoramidite Ligands and Chiral Brønsted Acids Derived from D-Mannitol." Int. J. Mol. Sci. 13, no. 3: 2727-2743.

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