Iodoarene derivative, method for manufacturing optically active spirolactone compound by using the same, and method for manufacturing optically active cycloadduct

摘要

An optically active spirolactone compound is highly enantioselectively produced by using an iodoarene derivative which can be synthesized easily and which is not racemized easily. A hypervalent iodine compound precursor (iodoarene derivative) which was able to be designed flexibly was synthesized from 2,6-dihydroxyiodoarene by using 1,2-aminoalcohol as a chiral source in short steps, a hypervalent iodine compound was prepared in a reaction system (in situ) by using a catalyst quantity of the resulting precursor in the presence of a stoichiometric quantity of m-CPBA, and a spirolactonization reaction of 3-(1-hydroxy-2-naphthyl)propionic acid was induced. As a result, a corresponding spirolactone compound was obtained at a high enantiomeric excess.;

主权项

1. An iodoarene derivative represented by Formula (a): where:
A represents a monovalent iodine atom or a trivalent iodine atom having two ligands,R1, R4, R5, and R8 represent a hydrogen atom,R2 and R6 represent an aryl group, an alkoxycarbonyl group, an arylcarbonyl group, or an arylsulfonyl group,R3 and R7 represent an alkyl group, and both configurations of asymmetric carbon atoms bonding to R3 and R7 are R or both the configurations are S, andZ represents a hydrogen atom or an alkyl group.