Synthesis 2014; 46(13): 1765-1772
DOI: 10.1055/s-0033-1341226
paper
© Georg Thieme Verlag Stuttgart · New York

One-Pot Parallel Synthesis Approach to Secondary Amines Based on the Reductive Amination of Ketones

Authors

  • Andrey V. Bogolubsky

    a   Enamine Ltd., 23 Matrosova Street, Kyiv, 01103, Ukraine   Fax: +380(44)5373253   Email: ysmoroz@mail.enamine.net
  • Yurii S. Moroz*

    a   Enamine Ltd., 23 Matrosova Street, Kyiv, 01103, Ukraine   Fax: +380(44)5373253   Email: ysmoroz@mail.enamine.net
    b   ChemBioCenter, Kyiv National Taras Shevchenko University, 61 Chervonotkatska Street, Kyiv, 02094, Ukraine
  • Sergey E. Pipko

    b   ChemBioCenter, Kyiv National Taras Shevchenko University, 61 Chervonotkatska Street, Kyiv, 02094, Ukraine
  • Dmitriy M. Panov

    a   Enamine Ltd., 23 Matrosova Street, Kyiv, 01103, Ukraine   Fax: +380(44)5373253   Email: ysmoroz@mail.enamine.net
  • Anzhelika I. Konovets

    a   Enamine Ltd., 23 Matrosova Street, Kyiv, 01103, Ukraine   Fax: +380(44)5373253   Email: ysmoroz@mail.enamine.net
    c   The Institute of High Technologies, Kyiv National Taras Shevchenko University, 4 Glushkov Street, Building 5, Kyiv, 03187, Ukraine
  • Roman Doroschuk

    d   Department of Chemistry, Kyiv National Taras Shevchenko University, 64 Volodymyrska Street, Kyiv, 01601, Ukraine
  • Andrey Tolmachev

    a   Enamine Ltd., 23 Matrosova Street, Kyiv, 01103, Ukraine   Fax: +380(44)5373253   Email: ysmoroz@mail.enamine.net
    b   ChemBioCenter, Kyiv National Taras Shevchenko University, 61 Chervonotkatska Street, Kyiv, 02094, Ukraine
Further Information

Publication History

Received: 05 February 2014

Accepted after revision: 21 March 2014

Publication Date:
11 April 2014 (online)


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Abstract

A combination of a condensation mixture [a Lewis acid, Ti(Oi-Pr)4, and a water scavenger, 1-(trimethylsilyl)-2-pyrrolidinone] and a simple reductant (NaBH4) provides an efficient one-pot approach to parallel synthesis of secondary amines by the reductive amination of ketones. The approach demonstrated its applicability to a variety of substrates with different degree of hindrance of an amino or a carbonyl group affording products in moderate to high yields.

Supporting Information