Catalytic Enantioselective Construction of All-Carbon Quaternary Stereocenters

Barry M. Trost; Chunhui Jiang

doi:10.1055/s-2006-926302

REVIEW

Catalytic Enantioselective Construction of All-Carbon Quaternary Stereocenters

Barry M. Trost*, Chunhui Jiang
Chemistry Department, Stanford University, Stanford, CA 94305, USA
Fax: +1(650)7250002; e-Mail: bmtrost@stanford.edu;

Abstract

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Abstract

Catalytic enantioselective construction of all-carbon quaternary stereocenters, i.e. carbon atoms bearing four different carbon substituents, poses a particular challenge in organic synthesis. This review gives a comprehensive account on the currently available methods of the above transformation that afford high enantioselectivities and synthetically useful yields.

1 Introduction
2 Cycloadditions
2.1 Diels-Alder Reactions
2.2 [3+2] Cycloadditions
2.3 [2+2] Synthesis of β-Lactams
2.4 Cyclopropanations
3 Combination of Carbon Nucleophiles and Carbon Electrophiles
3.1 Michael Additions and Direct Alkylations
3.2 Allylation via Palladium π-Allyl Intermediates
3.3 Copper-Catalyzed S_N2′ Allylations
3.4 Reactions with Carbonyl and Imine Electrophiles
4 Arylation and Vinylation Reactions
4.1 Intramolecular Heck Reactions
4.2 α-Arylation and Vinylation Reactions of Ketones and Lactones
4.3 Desymmetrizing Suzuki Couplings
5 Metal-Catalyzed Diene and Enyne Cyclizations
5.1 Diene Cyclizations
5.2 Enyne Cyclizations
6 Intramolecular Hydroacylations
6.1 Intramolecular Stetter Reactions
6.2 Rhodium-Catalyzed Desymmetrization
7 Allylations Mediated by Tertiary Radicals or Cations
8 Rhodium-Catalyzed C-H Insertions
9 Other Desymmetrization Methods
10 Summary and Outlook

Key words

asymmetric catalysis - asymmetric synthesis - chirality - enantioselectivity - quaternary stereocenters

Full Text

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