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The boronic acid Mannich reaction

Journal Article


Abstract


  • The boronic acid Mannich reaction is a three-component reaction between a carbonyl compound (aldehyde or ketone), an amine (primary or secondary) and a boronic acid. This chapter addresses the mechanism, stereochemistry, and the scope and limitations of each of the three components of this reaction. Some typical experimental conditions are provided along with a comprehensive Tabular Survey.

    This three-component reaction is extremely versatile for preparing important chiral starting materials for the synthesis of molecules of biological interest, including chiral α-amino acids, 1,2-amino alcohols, 2-aminoalkyl phenols, heterocycles, and alkaloids as shown in the general scheme below.

    This chapter addresses the mechanism, stereochemistry, and the scope and

    limitations of each of the three components of the boronic acid Mannich reaction.

    Some typical experimental conditions are provided along with a comprehensive

    Tabular Survey in which reactions have been classified on the basis of the types

    of products that are formed.

    The Tabular Survey includes the literature from the period 1993 to 2011.

    Supplemental references are provided in the bibliography for reactions reported

    in 2012 and in 2013 (up to the date of submission). Several other reviews on the

    boronic acid Mannich reaction have been published.

UOW Authors


Publication Date


  • 2014

Citation


  • Pyne, S. G. & Tang, M. (2014). The boronic acid Mannich reaction. Organic Reactions, 83 211-498.

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/1932

Number Of Pages


  • 287

Start Page


  • 211

End Page


  • 498

Volume


  • 83

Place Of Publication


  • http://onlinelibrary.wiley.com/book/10.1002/0471264180

Abstract


  • The boronic acid Mannich reaction is a three-component reaction between a carbonyl compound (aldehyde or ketone), an amine (primary or secondary) and a boronic acid. This chapter addresses the mechanism, stereochemistry, and the scope and limitations of each of the three components of this reaction. Some typical experimental conditions are provided along with a comprehensive Tabular Survey.

    This three-component reaction is extremely versatile for preparing important chiral starting materials for the synthesis of molecules of biological interest, including chiral α-amino acids, 1,2-amino alcohols, 2-aminoalkyl phenols, heterocycles, and alkaloids as shown in the general scheme below.

    This chapter addresses the mechanism, stereochemistry, and the scope and

    limitations of each of the three components of the boronic acid Mannich reaction.

    Some typical experimental conditions are provided along with a comprehensive

    Tabular Survey in which reactions have been classified on the basis of the types

    of products that are formed.

    The Tabular Survey includes the literature from the period 1993 to 2011.

    Supplemental references are provided in the bibliography for reactions reported

    in 2012 and in 2013 (up to the date of submission). Several other reviews on the

    boronic acid Mannich reaction have been published.

UOW Authors


Publication Date


  • 2014

Citation


  • Pyne, S. G. & Tang, M. (2014). The boronic acid Mannich reaction. Organic Reactions, 83 211-498.

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/1932

Number Of Pages


  • 287

Start Page


  • 211

End Page


  • 498

Volume


  • 83

Place Of Publication


  • http://onlinelibrary.wiley.com/book/10.1002/0471264180