Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 New mechanistic studies on the proline-catalyzed aldol reaction.

Literature DB >> 15073330

New mechanistic studies on the proline-catalyzed aldol reaction.

Benjamin List¹, Linh Hoang, Harry J Martin.

Abstract

The mechanism of the proline-catalyzed aldol reaction has stimulated considerable debate, and despite limited experimental data, at least five different mechanisms have been proposed. Complementary to recent theoretical studies we have initiated an experimental program with the goal of clarifying some of the basic mechanistic questions concerning the proline-catalyzed aldol reaction. Here we summarize our discoveries in this area and provide further evidence for the involvement of enamine intermediates.

Entities: Chemical

Mesh：

Substances：

Year: 2004 PMID： 15073330 PMCID： PMC395996 DOI： 10.1073/pnas.0307979101

Source DB: PubMed Journal: Proc Natl Acad Sci U S A ISSN： 0027-8424 Impact factor: 11.205

16 in total

1. Enantioselective Organocatalysis.

Authors: Peter I. Dalko; Lionel Moisan
Journal: Angew Chem Int Ed Engl Date: 2001-10-15 Impact factor: 15.336

2. The first direct and enantioselective cross-aldol reaction of aldehydes.

Authors: Alan B Northrup; David W C MacMillan
Journal: J Am Chem Soc Date: 2002-06-19 Impact factor: 15.419

3. Kinetic and stereochemical evidence for the involvement of only one proline molecule in the transition states of proline-catalyzed intra- and intermolecular aldol reactions.

Authors: Linh Hoang; S Bahmanyar; K N Houk; Benjamin List
Journal: J Am Chem Soc Date: 2003-01-08 Impact factor: 15.419

New mechanistic studies on the proline-catalyzed aldol reaction.

1. Enantioselective Organocatalysis.

2. The first direct and enantioselective cross-aldol reaction of aldehydes.

3. Kinetic and stereochemical evidence for the involvement of only one proline molecule in the transition states of proline-catalyzed intra- and intermolecular aldol reactions.

4. Direct catalytic asymmetric aldol reactions of aldehydes.

5. Nonlinear effects in asymmetric synthesis. Examples in asymmetric oxidations and aldolization reactions.

6. Immune versus natural selection: antibody aldolases with enzymic rates but broader scope.

7. Efficient proline-catalyzed Michael additions of unmodified ketones to nitro olefins.

8. Direct catalytic asymmetric alpha-amination of aldehydes.

9. Intermolecular alkyl radical addition to chiral N-acylhydrazones mediated by manganese carbonyl.

10. Catalytic asymmetric intramolecular alpha-alkylation of aldehydes.

Review 1. The direct catalytic asymmetric aldol reaction.

Review 2. Quantum mechanical investigations of organocatalysis: mechanisms, reactivities, and selectivities.

3. L-Proline Functionalized Polymers Prepared by RAFT Polymerization and Their Assemblies as Supported Organocatalysts.

4. Solid-Phase Synthesis of β-Hydroxy Ketones Via DNA-Compatible Organocatalytic Aldol Reactions.

5. Developing novel organocatalyzed aldol reactions for the enantioselective synthesis of biologically active molecules.

6. Caged Proline in Photoinitiated Organocatalysis.

7. Asymmetric aza-[3+3] annulation in the synthesis of indolizidines: an unexpected reversal of regiochemistry.

8. Crystal structures of proline-derived enamines.

Review 9. Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.

10. Rate limiting step precedes C-C bond formation in the archetypical proline-catalyzed intramolecular aldol reaction.