ChemInform Abstract: Novel Enantioselective Acylating Agents. The Reactions of Chiral Orthoesters and Silyl Enol Ethers as a Route to Optically Active Monoprotected 1,3-Dicarbonyl Compounds.

ChemInform ◽  
1990 ◽  
Vol 21 (48) ◽  
Author(s):  
T. BASILE ◽  
L. LONGOBARDO ◽  
E. TAGLIAVINI ◽  
C. TROMBINI ◽  
A. UMANI-RONCHI
1997 ◽  
Vol 75 (7) ◽  
pp. 965-974 ◽  
Author(s):  
M. Anne Charlton ◽  
James R. Green

Ester-substituted allyltetracarbonyliron cations react with cycloalkylidene-type silyl enol ethers, silyl ketene acetals, and β-keto-esters to give 1,6-dicarbonyl compounds containing a newly formed quaternary centre. Selected condensation products are converted by enolate chemistry into spirocyclic [4.4], [4.5], and [4.6] systems. Acyloin and other reductive cyclization reactions are employed to convert the condensation products into spirocyclic [4.5], [5.5], and [5.6] systems. Keywords: allyliron complexes, umpolung synthesis, 1,6-dicarbonyls, spirocycle synthesis.


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