Application of cis-2-amino-3,3-dimethyl-1-indanol as an efficient chiral auxiliary to the asymmetric Ireland-Claisen rearrangement. Improvement of the diastereoselectivity by combinational use of chlorodimethylsilane as a silylating agent

The asymmetric Ireland-Claisen rearrangement of allyl carboxylates having a chiral substituent at the alpha-position of the carboxylate part gave the desired products with excellent diastereoselectivity, when an oxazolidinone , which was prepared from a non-natural chiral auxiliary, (1R,2S)-cis-2-ami no-3,3-dimethyl-1-indanol, was used as the chiral substituent. Furthermore, the diastereoselectivity was improved by using chlorodimethylsilane as a s ilylating agent of the intermediary enolates.