Diastereoselective Temporary Silicon-Tethered Ring-Closing-Metathesis Reactions with Prochiral Alcohols: A New Approach to Long-Range Asymmetric Induction

A useful approach to 1,4‐, 1,5‐, and 1,6‐stereocontrol, diastereoselective ring‐closing‐metathesis reactions that utilize temporary silicon tethers represent a new strategy for long‐range asymmetric induction. This method facilitates the construction of cis‐1,4‐silaketals (n=0, d.r.=20:1; see scheme...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2003-04, Vol.42 (15), p.1734-1737
Main Authors: Evans, P. Andrew, Cui, Jian, Buffone, Gerald P.
Format: Article
Language:English
Subjects:
Alcohols - chemistry
Catalysis
Cyclization
diastereoselectivity
Heterocyclic Compounds, 1-Ring - chemical synthesis
Heterocyclic Compounds, 1-Ring - chemistry
Kinetics
medium-sized rings
metathesis
Si-Tethered Asymmetric Induction
Silanes - chemistry
silicon
Silicon - chemistry
Stereoisomerism
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Summary:A useful approach to 1,4‐, 1,5‐, and 1,6‐stereocontrol, diastereoselective ring‐closing‐metathesis reactions that utilize temporary silicon tethers represent a new strategy for long‐range asymmetric induction. This method facilitates the construction of cis‐1,4‐silaketals (n=0, d.r.=20:1; see scheme), whereas the extension of this concept to higher alkenyl alcohols (n=1–4) results in a reversal of diastereoselectivity that favors formation of the trans isomer.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200250486