Catalytic asymmetric direct Mannich reaction: a powerful tool for the synthesis of α,β-diamino acids
Top Cited Papers
- 14 April 2009
- journal article
- review article
- Published by Royal Society of Chemistry (RSC) in Chemical Society Reviews
- Vol. 38 (7), 1940-1948
- https://doi.org/10.1039/b820303b
Abstract
Optically active α,β-diamino acids are very attractive targets in organic synthesis because of their wide-ranging biological significance and high versatility as synthetic building blocks. Efficient synthesis of such non-proteinogenic amino acid derivatives must face the challenge of generating two contiguous stereocenters with complete diastereo- and enantiocontrol in flexible, acyclic molecules. The catalytic asymmetric direct Mannich reaction has provided elegant and efficient solutions for the stereocontrolled assembly of both syn- and anti-α,β-diamino acid derivatives, including those with a α-tetrasubstituted carbon stereocenter, with the aid of either organometallic or purely organic chiral catalysts (or the combination of both). This tutorial review highlights progress in this area, which has recently been boosted through two complementary strategies: the direct Mannich reaction of glycine ester Schiff bases with imines and the direct aza-Henry reaction between nitro compounds and imines.Keywords
This publication has 38 references indexed in Scilit:
- Organocatalytic Asymmetric Mannich Reactions: New Methodology, Catalyst Design, and Synthetic ApplicationsEuropean Journal of Organic Chemistry, 2007
- Organocatalysed asymmetric Mannich reactionsChemical Society Reviews, 2007
- Enantioselective Diamination of Alkenes by Use of a Bisimidoosmium Reagent with the Aid of Chiral CatalystsEuropean Journal of Organic Chemistry, 2006
- Catalytic Enantioselective Construction of All-Carbon Quaternary StereocentersSynthesis, 2006
- α,β-Diamino Acids: Biological Significance and Synthetic ApproachesChemical Reviews, 2005
- Enantioselective catalytic diamination of alkenes with a bisimidoosmium oxidantChemical Communications, 2005
- Asymmetric Strecker Route toward the Synthesis of Biologically Active α,α-Disubstituted α-Amino AcidsBulletin of the Chemical Society of Japan, 2003
- Expedient Asymmetric Synthesis of All Four Isomers of N,N‘-Protected 2,3-Diaminobutanoic AcidThe Journal of Organic Chemistry, 2001
- Stereoselective synthesis of quaternary α-amino acids. Part 1: Acyclic compoundsTetrahedron: Asymmetry, 1998
- Asymmetric hydrogenation of (E)-α,β-bis(N-acylamino)acrylates catalyzed by a rhodium complex with trans-chelating chiral diphosphine ligandTetrahedron: Asymmetry, 1998