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. 2012 Oct 10;134(40):16449-51.
doi: 10.1021/ja305448w. Epub 2012 Sep 24.

Direct stereospecific amination of alkyl and aryl pinacol boronates

Scott N Mlynarski  1 , Alexander S Karns, James P Morken
Affiliations

Direct stereospecific amination of alkyl and aryl pinacol boronates

Scott N Mlynarski et al. J Am Chem Soc. .

Abstract

The direct amination of alkyl and aryl pinacol boronates is accomplished with lithiated methoxyamine. This reaction directly provides aliphatic and aromatic amines, stereospecifically, and without preactivation of the boronate substrate.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1
See this image and copyright information in PMC

References

    1. Reviews: Brown HC, Kramer GW, Levy AB, Midland MM. Organic Syntheses via Boranes. Wiley-Interscience; New York: 1975. Brown HC, Singaram B. Acc Chem Res. 1988;21:287.Crudden CM, Edwards D. Eur J Org Chem. 2003:4695.

    1. For recent examples of aminations that are either not stereospecific, or where stereochemistry was not studied or not an issue, see: Ou L, Shao J, Zhang G, Yu Y. Tetrahedron Lett. 2011;52:1430.Matsuda N, Hirano K, Satoh T, Miura M. Angew Chem Int Ed. 2012;51:3642.Larrosa M, Guerrero C, Rodríguez R, Cruces J. Synlett. 2010:2101.Cazorla C, Métay E, Andrioletti B, Lemaire M. Tetrahedron Lett. 2009;50:6855.Rucker RP, Whittaker AM, Dang H, Lalic G. J Am Chem Soc. 2012;134:6571.

    1. Brown HC, Midland MM, Levy AB. J Am Chem Soc. 1973;95:2394.
    2. Brown HC, Salunkhe AM, Argade AB. Organometallics. 1992;11:3094.
    3. Carboni B, Vaultier M, Carrie R. Tetrahedron. 1987;43:1799.
    4. Carboni B, Vaultier M, Carrie R. Tetrahedron Lett. 1988;29:1279.
    5. Hupe E, Marek I, Knochel P. Org Lett. 2002;4:2861. - PubMed
    1. Matteson DS, Kim GY. Org Lett. 2002;4:2153. - PubMed
    2. Kim BJ, Matteson DS. Angew Chem Int Ed. 2004;43:3056. - PubMed
    3. Bagutski V, Elford TG, Aggarwal VK. Angew Chem Int Ed. 2011;50:1080. - PubMed
    1. Brown HC, Kim KW, Cole TE, Singaram B. J Am Chem Soc. 1986;108:6761.

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