Beilstein J. Org. Chem.2023,19, 719–726, doi:10.3762/bjoc.19.52
imine species provide a very flexible approach to the arylglycine scaffold [2][9]. The Petasisborono-Mannich reaction constitutes a prominent example for such an imine-based multicomponent reaction (Scheme 1a). The reaction of glyoxylic acid, an amine component and an arylboronic acid offers a highly
modular access to arylglycines from three readily available building blocks [10][11][12]. The Petasisborono-Mannich reaction usually proceeds in the absence of any external catalyst via zwitterionic intermediates and an intramolecular transfer of the aryl residue form the activated boronate to the
electrophilic iminium carbon, leading to the amine product as racemic mixture. Consequently, examples for asymmetric Petasisborono-Mannich reactions are rare [13] and usually rely on the utilization of chiral amine components in stoichiometric amounts [10][11].
As part of our research program utilizing the in
PDF
Graphical Abstract
Figure 1:
Biologically active molecules containing α-arylglycine motifs (highlighted in green and blue).
Beilstein J. Org. Chem.2014,10, 237–250, doi:10.3762/bjoc.10.19
tools in synthetic organic chemistry. The most significant recent results and developments obtained in this area are reported in this review.
Keywords: allylboration; boron compounds; Diels–Alder; 1,3-dienes; multicomponent reactions; Petasisborono–Mannich; Suzuki couplings; Introduction
and (E)-styrylboronic acid [12]. This was the first report of this type of transformation, which is now referred as the Petasisborono–Mannich reaction, and was later extended to a wide variety of other aldehydes, such as glyoxylic acid (for example), boronic acids, esters or trifluoroborates and
sequence.
A two-step reaction sequence for the synthesis of tetrahydronaphthalenes 12.
Tandem sequence based on the Petasisborono–Mannich reaction as first key step.
One-pot tandem dimerization/allylboration reaction of 1,3-diene-2-boronate.
Tandem Diels–Alder/cross-coupling reactions of trifluoroborates
PDF
Graphical Abstract
Scheme 1:
1-Boron-substituted 1,3-diene in a tandem cycloaddition [4 + 2]/allylboration sequence.