(2 R ,2′ R )‐2,2′‐[(2‐Iodo‐1,3‐phenylene)bis(oxy)]bis[ N ‐(2,4,6‐trimethylphenyl)propanamide]

Abstract

image [1226896‐38‐3] C 30 H 35 IN 2 O 4 (MW 614.5245) InChI = 1S/C30H35IN2O4/c1‐16‐12‐18(3)27(19(4)13‐16)32‐29(34)22(7)36‐24‐10‐9‐11‐25(26(24)31)37‐23(8)30(35)33‐28‐20(5)14‐17(2)15‐21(28)6/h9‐15,22‐23H,1‐8H3,(H,32,34)(H,33,35)/t22‐,23‐/m1/s1 InChiKey = ZVOKSLMZXDIXPR‐DHIUTWEWSA‐N (catalyst for oxidative coupling reactions, 1–3 the precursor of chiral organoiodine(III) reagent 1–3 ) Alternative Names : ( R , R )‐2‐Iodo‐1,3‐bis[1‐(mesitylcarbamoyl)ethoxy]benzene. Physical Data : –116.1° ( c 1.0, CHCl 3 ). 4 Solubility : soluble in most organic solvents except hydrocarbons (e.g., hexane) and diethyl ether. Form Supplied in : white to off‐white crystal. Handling, Storage, and Precautions : light, air, and heat sensitive. Store under inert gas in a dark place at 2–10 °C. Preparation : (2 R ,2′ R )‐2,2′‐[(2‐Iodo‐1,3‐phenylene)bis(oxy)]bis[ N ‐(2,4,6‐trimethylphenyl)propanamide], ( R , R )‐ 1a , can be prepared from 2‐iodoresorcinol in three steps (eq 1). 4,5 The Mitsunobu reaction of 2‐iodoresorcinol with (–)‐ethyl lactate affords C 2 ‐symmetric bisester. Hydrolysis followed by dichlorination with thionyl chloride, and diamidation via mesitylamine gives ( R , R )‐ 1a . ( R , R )‐ 1a is commercially available from FUJIFILM Wako Pure Chemical Corporation, and Tokyo Chemical Industry Co., Ltd. image