1,n-Glycols as Dialdehyde Equivalents in Iridium-Catalyzed Enantioselective Carbonyl Allylation and Iterative Two-Directional Assembly of 1,3-Polyols

1,n-Glycols as Dialdehyde Equivalents in Iridium-Catalyzed Enantioselective Carbonyl Allylation and Iterative Two-Directional Assembly of 1,3-Polyols

Unstable? We're able! 1,n-Glycols serve as synthetic equivalents to unstable dialdehydes in two-directional carbonyl allylation from the alcohol oxidation level under iridium-catalyzed transfer hydrogenation conditions. Iterative asymmetric allylation employing 1,3-propanediol enables the rapid...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2009-01, Vol.48 (27), p.5018-5021
Hauptverfasser: Lu, Yu, Kim, In Su, Hassan, Abbas, Del Valle, David J, Krische, Michael J
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
allylation
Catalysis
diols
enantioselectivity
Hydrogenation
iridium
Iridium - chemistry
Oxidation-Reduction
Polymers - chemical synthesis
Polymers - chemistry
Stereoisomerism
transfer hydrogenation
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Zusammenfassung:Unstable? We're able! 1,n-Glycols serve as synthetic equivalents to unstable dialdehydes in two-directional carbonyl allylation from the alcohol oxidation level under iridium-catalyzed transfer hydrogenation conditions. Iterative asymmetric allylation employing 1,3-propanediol enables the rapid assembly of protected 1,3-polyol substructures with exceptional levels of stereocontrol.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200901648