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-amino-3,3-dimethyl-l-indanol, was used as the chiral substituent. Furthermore, the diastereoselectivity was improved by using chlorodimethylsilane as a silylating agent of the intermediary enolates.
Matsui
S
Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, Japan.
Oka
N
Hashimoto
Y
Saigo
K