Asymmetric Michael Reaction of Acetaldehyde Catalyzed by Diphenylprolinol Silyl Ether

Asymmetric Michael Reaction of Acetaldehyde Catalyzed by Diphenylprolinol Silyl Ether

An acetaldehyde breakthrough: The catalytic asymmetric Michael addition reaction of acetaldehyde and various nitroalkenes in the presence of a chiral diphenylprolinol silyl ether organocatalyst is described (see scheme; TMS=trimethylsilyl). The desired 1,4‐addition products, α‐unsubstituted γ‐nitro...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2008-06, Vol.47 (25), p.4722-4724
Hauptverfasser: Hayashi, Yujiro, Itoh, Takahiko, Ohkubo, Masahiro, Ishikawa, Hayato
Format: Artikel
Sprache:eng
Schlagworte:
acetaldehyde
Acetaldehyde - chemistry
asymmetric catalysis
Catalysis
Ethers - chemistry
Michael addition
Molecular Structure
Proline - analogs & derivatives
Proline - chemistry
Solvents - chemistry
Stereoisomerism
Styrenes - chemistry
synthetic methods
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Zusammenfassung:An acetaldehyde breakthrough: The catalytic asymmetric Michael addition reaction of acetaldehyde and various nitroalkenes in the presence of a chiral diphenylprolinol silyl ether organocatalyst is described (see scheme; TMS=trimethylsilyl). The desired 1,4‐addition products, α‐unsubstituted γ‐nitro aldehydes, were obtained in good yields with excellent enantioselectivities.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200801130