Alternative synthetic route to chiral N-substituted camphor-derived beta-amino alcohols.
An alternative route from (1R)-(+)-camphor to chiral N-substituted camphor-derived beta-amino alcohol (4b-e) consists of four steps with a total yield of 28%. N-Alkylation of camphor-derived beta-amino alcohol (4a) involves condensation and hydride reduction in one pot without isolation of intermediates. Condensation of 4a with aldehydes or ketones generates a mixture of 1,3-oxazolidines (6) and imino-alcohols (7), which are reduced to 4b-e by NaBH(4).
Cheng
Gin-Ian
GI
Department of Chemistry, National Cheng Kung University, Tainan, Taiwan, Republic of China.
Shei
Chun-Tin
CT
Sung
Kuangsen
K