2016 年 74 巻 3 号 p. 233-242
This article highlights my recent studies on development of optically active hypervalent iodine(III) reagents which have a chiral side chain derived from lactic acid. The lactate chiral side chain may nucleophilically interact with the iodine atom, and the interaction induces pseudo chirality of the iodine atom. Owing to the pseudo chirality, the iodine(III) reagent is able to highly distinguish the enantioface of an alkene substrate. Actually, the lactate-based hypervalent iodine(III) reagents have been used for various types of enantioselective oxidation leading to high ee. One of the stereoselective oxidations is applied to a crucial step for the asymmetric synthesis of 4-oxyisochroman-1-one natural products.