864058-51-5Relevant articles and documents
Synthesis and evaluation of 7-hydroxyindan-1-one-derived chiral auxiliaries
Narine, Arun A.,Wilson, Peter D.
, p. 413 - 419 (2007/10/03)
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, CH 2O(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 Diels-Alder 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.