Enantiodifferentiating endo-Selective Oxylactonization of ortho-Alk-1-enylbenzoate with a Lactate-Derived Aryl-λ3-Iodane


  • We are very grateful to Dr. Hiroki Akutsu and Prof. Shin′ichi Nakatsuji (Hyogo) for X-ray crystallographic analyses and to Prof. Tadashi Okuyama (Hyogo) for reading this manuscript.


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It's the hype: The asymmetric synthesis of 3-alkyl-4-oxyisochroman-1-one is achieved by oxylactonization of ortho-alk-1-enylbenzoate with a series of optically active hypervalent iodine(III) reagents prepared from lactate or valine as a chiral source (see scheme). The oxylactonization is highly regio-, diastereo-, and enantioselective.