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- W4313650764 abstract "The fluorine atom is a powerful, yet enigmatic influence on chemical reactions. True to form, fluorine was recently discovered to effect diastereodivergence in an enantioselective aza-Henry reaction, resulting in a very rare case of syn-β-amino nitroalkane products. More bewildering was the observation of an apparent hierarchy of substituents within this substrate-controlled behavior: Ph>F>alkyl. These cases have now been examined comprehensively by computational methods, including both non-fluorinated and α-fluoro nitronate additions to aldimines catalyzed by a chiral bis(amidine) [BAM] proton complex. This study revealed the network of non-covalent interactions that dictate anti- (α-aryl) versus syn-selectivity (α-alkyl) using α-fluoronitronate nucleophiles, and an underlying secondary orbital interaction between fluorine and the activated azomethine." @default.
- W4313650764 created "2023-01-07" @default.
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- W4313650764 date "2023-03-20" @default.
- W4313650764 modified "2023-09-26" @default.
- W4313650764 title "Secondary Orbital Effect Involving Fluorine is Responsible for Substrate‐Controlled Diastereodivergence in the Catalyzed <i>syn‐</i>aza‐Henry Reaction of α‐Fluoronitroalkanes" @default.
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- W4313650764 doi "https://doi.org/10.1002/chem.202204066" @default.
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