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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
Author(s) -
Annunziata Rita,
Benaglia Maurizio,
Cinquini Mauro,
Cozzi Franco,
Raimondi Laura
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199809)1998:9<1823::aid-ejoc1823>3.0.co;2-h
Subject(s) - chemistry , alkoxy group , stereoselectivity , nitrile , cycloaddition , computational chemistry , dipole , nitrone , 1,3 dipolar cycloaddition , organic chemistry , catalysis , alkyl
The 1,3‐dipolar cycloaddition of formaldehyde N ‐benzylnitrone with β′‐alkoxy‐ and γ‐alkoxy‐α,β‐unsaturated esters was investigated. The stereochemical outcome of these reactions was nicely rationalized on the basis of an interpretation of the inside alkoxy theory emphasizing the electrostatic interactions in the reaction TS. The force field approach previously developed for evaluating the stereoselection in nitrile oxide cycloadditions to chiral alkenes was successfully extended to nitrones′ reactions.