How to Make Five Contiguous Stereocenters in One Reaction: Asymmetric Organocatalytic Synthesis of Pentasubstituted Cyclohexanes

How to Make Five Contiguous Stereocenters in One Reaction: Asymmetric Organocatalytic Synthesis of Pentasubstituted Cyclohexanes

Give me five! An organocatalyzed two‐component domino reaction has been developed in which two new CC bonds and five stereocenters are created in a one‐pot fashion (see scheme; DABCO=1,4‐diazabicyclo[2.2.2]octane, TMS=trimethylsilyl). The striking features of this transformation are the high prefer...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2007-01, Vol.46 (48), p.9202-9205
Hauptverfasser: Reyes, Efraím, Jiang, Hao, Milelli, Andrea, Elsner, Petteri, Hazell, Rita G, Jørgensen, Karl Anker
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Alkanes - chemistry
asymmetric synthesis
Catalysis
Cyclohexanes - chemical synthesis
Cyclohexanols - chemistry
domino reaction
nucleophilic addition
organocatalysis
α,β‐unsaturated aldehydes
β-unsaturated aldehydes
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Zusammenfassung:Give me five! An organocatalyzed two‐component domino reaction has been developed in which two new CC bonds and five stereocenters are created in a one‐pot fashion (see scheme; DABCO=1,4‐diazabicyclo[2.2.2]octane, TMS=trimethylsilyl). The striking features of this transformation are the high preference for one diastereomer (out of 32 possible isomers) and enantioselectivities of up to 94 %.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200704454