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).

Oxidation O 0212TiCl4/tert-Butyl Hydroperoxide: Chemioselective Oxidation of Secondary Alcohols and Suppression of Sharpless Epoxidation. -In the presence of TBHP and catalytic amounts of TiCl4, secondary alcohols undergo chemoselective oxidation to ketones. Primary alcohols and C=C double bonds are not attacked. The 1,3-diol (IIIb) yields exclusively the hydroxyl ketone (IVb) and starting from 1,2-diols no ketones are obtained.