中文名称 | 英文名称 | CAS号 | 化学式 | 分子量 |
---|---|---|---|---|
7-羟基-1-茚酮 | 7-hydroxy-indan-1-one | 6968-35-0 | C9H8O2 | 148.161 |
A series of novel chiral acetals were prepared from 7-hydroxyindan-1-one and a variety of substituted chiral nonracemic C2-symmetric 1,2-ethanediols (R = Me, Ph, CH2OMe, CH2OBn, CH2O(1-Np), and i-Pr). These acetals were evaluated as chiral auxiliaries for use in asymmetric synthesis. A high degree of stereochemical induction was observed in the diethylaluminum chloride-promoted DielsAlder reaction of an acrylate derivative (R = i-Pr) with cyclopentadiene (91:9 dr). This demonstrated that these acetals could serve as effective chiral directors in asymmetric substrate-directed reactions.Key words: 7-hydroxyindan-1-one, chiral nonracemic C2-symmetric 1,2-diols, acetals, chiral auxiliaries, DielsAlder reaction.