Metal-Catalyzed Regiodivergent Cyclization of γ-Allenols: Tetrahydrofurans versus Oxepanes

Ringing the changes: The 5‐exo‐trig cyclization pathway of γ‐allenols can be completely reversed by either changing the metal (Pd instead of Au) or using a (methoxymethyl)oxy protecting group. As a result, the 7‐endo‐trig alkoxycyclization dominates instead (see scheme; MOM=MeOCH2; Z1=tBuMe2Si, ArCO...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2007-01, Vol.46 (35), p.6684-6687
Main Authors: Alcaide, Benito, Almendros, Pedro, Martínez del Campo, Teresa
Format: Article
Language:English
Subjects:
Alcohols - chemistry
Alkadienes - chemistry
allenes
Bridged Bicyclo Compounds - chemistry
Catalysis
Cyclization
Deuterium Oxide - chemistry
Ethers, Cyclic - chemistry
Furans - chemistry
gold
Gold - chemistry
heterocycles
Indicators and Reagents
Metals - chemistry
palladium
Palladium - chemistry
regioselectivity
Stereoisomerism
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Summary:Ringing the changes: The 5‐exo‐trig cyclization pathway of γ‐allenols can be completely reversed by either changing the metal (Pd instead of Au) or using a (methoxymethyl)oxy protecting group. As a result, the 7‐endo‐trig alkoxycyclization dominates instead (see scheme; MOM=MeOCH2; Z1=tBuMe2Si, ArCO).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200701611