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Synthesis 2006(3): 369-396
DOI: 10.1055/s-2006-926302
DOI: 10.1055/s-2006-926302
REVIEW
© Georg Thieme Verlag Stuttgart · New York
Catalytic Enantioselective Construction of All-Carbon Quaternary Stereocenters
Further Information
Received
18 August 2005
Publication Date:
13 January 2006 (online)
Publication History
Publication Date:
13 January 2006 (online)
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.
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1 Introduction
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2 Cycloadditions
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2.1 Diels-Alder Reactions
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2.2 [3+2] Cycloadditions
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2.3 [2+2] Synthesis of β-Lactams
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2.4 Cyclopropanations
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3 Combination of Carbon Nucleophiles and Carbon Electrophiles
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3.1 Michael Additions and Direct Alkylations
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3.2 Allylation via Palladium π-Allyl Intermediates
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3.3 Copper-Catalyzed SN2′ Allylations
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3.4 Reactions with Carbonyl and Imine Electrophiles
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4 Arylation and Vinylation Reactions
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4.1 Intramolecular Heck Reactions
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4.2 α-Arylation and Vinylation Reactions of Ketones and Lactones
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4.3 Desymmetrizing Suzuki Couplings
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5 Metal-Catalyzed Diene and Enyne Cyclizations
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5.1 Diene Cyclizations
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5.2 Enyne Cyclizations
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6 Intramolecular Hydroacylations
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6.1 Intramolecular Stetter Reactions
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6.2 Rhodium-Catalyzed Desymmetrization
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7 Allylations Mediated by Tertiary Radicals or Cations
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8 Rhodium-Catalyzed C-H Insertions
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9 Other Desymmetrization Methods
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10 Summary and Outlook
Key words
asymmetric catalysis - asymmetric synthesis - chirality - enantioselectivity - quaternary stereocenters
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