Hydrogen Bond Catalyzed Enantioselective Vinylogous Mukaiyama Aldol Reaction

Hydrogen Bond Catalyzed Enantioselective Vinylogous Mukaiyama Aldol Reaction

The concept of hydrogen bonding catalysis was extended to the vinylogous Mukaiyama aldol reaction, which gives rapid access to polyketide derivatives. The reaction of the silyldienol ether shown and a range of aldehydes catalyzed by TADDOL proceeds regiospecifically to produce the addition products...

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Veröffentlicht in:Organic letters 2005-12, Vol.7 (25), p.5657-5660
Hauptverfasser: Gondi, Vijaya Bhasker, Gravel, Michel, Rawal, Viresh H
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Catalysis
Hydrogen Bonding
Macrolides - chemical synthesis
Models, Molecular
Molecular Structure
Silanes - chemistry
Stereoisomerism
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Zusammenfassung:The concept of hydrogen bonding catalysis was extended to the vinylogous Mukaiyama aldol reaction, which gives rapid access to polyketide derivatives. The reaction of the silyldienol ether shown and a range of aldehydes catalyzed by TADDOL proceeds regiospecifically to produce the addition products in good yields and enantiomeric excesses.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol052301p