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The Importance of Electrostatic Interactions in the Stereoselective 1,3-Dipolar Cycloadditions of Nitrones to Chiral Allyl Ethers: An Experimental and Force Field Approach

✍ Scribed by Rita Annunziata; Maurizio Benaglia; Mauro Cinquini; Franco Cozzi; Laura Raimondi

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 617 KB
Volume: 1998
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(199809)1998:9<1823::aid-ejoc1823>3.0.co;2-h

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✦ Synopsis

The 1,3-dipolar cycloaddition of formaldehyde N-electrostatic interactions in the reaction TS. The force field approach previously developed for evaluating the benzylnitrone with βЈ-alkoxyand γ-alkoxy-α,β-unsaturated esters was investigated. The stereochemical outcome of stereoselection in nitrile oxide cycloadditions to chiral alkenes was successfully extended to nitronesЈ reactions. these reactions was nicely rationalized on the basis of an interpretation of the inside alkoxy theory emphasizing the

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