Title

The boronic acid Mannich reaction

RIS ID

90456

Publication Details

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

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.

Please refer to publisher version or contact your library.

Share

COinS
 

Link to publisher version (DOI)

http://dx.doi.org/10.1002/0471264180.or083.02