Diastereoselective and Enantioselective Synthesis of Tertiary α-Hydroxy Phosphonates through Hydrogen-Bond Catalysis

Diastereoselective and Enantioselective Synthesis of Tertiary α-Hydroxy Phosphonates through Hydrogen-Bond Catalysis

Hydrogen‐bond activation by a diol promotes enantioselective Mukaiyama aldol reactions of acyl phosphonates. This mild and general method gives α‐hydroxy phosphonate products having two chiral centers, one tertiary and one quaternary, formed with high diastereo‐ and enantioselectivity.

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Bibliographische Detailangaben
Veröffentlicht in:Angewandte Chemie (International ed.) 2009-01, Vol.48 (4), p.776-779
Hauptverfasser: Gondi, Vijaya Bhasker, Hagihara, Koji, Rawal, Viresh H
Format: Artikel
Sprache:eng
Schlagworte:
aldol reaction
brønsted acid catalysis
Catalysis
Crystallography, X-Ray
Dioxolanes - chemistry
enantioselectivity
Hydrogen Bonding
hydrogen bonds
Methanol - analogs & derivatives
Methanol - chemistry
Organophosphonates - chemical synthesis
Organophosphonates - chemistry
phosphonates
Stereoisomerism
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Beschreibung
Zusammenfassung:Hydrogen‐bond activation by a diol promotes enantioselective Mukaiyama aldol reactions of acyl phosphonates. This mild and general method gives α‐hydroxy phosphonate products having two chiral centers, one tertiary and one quaternary, formed with high diastereo‐ and enantioselectivity.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200804244