Aminobicyclo[2,2,1]heptanes. Part II. Diastereoisomeric dimethylaminobornyl acetates

Alternative synthetic route to chiral N‐substituted camphor‐derived β‐amino alcohols

“…This result is consistent with the ones obtained by Thornton 23 and Tanaka 25 but contrary to the reports of other groups. [43][44][45] As a result, we reduced the two functional groups in 2 sequentially. As Thornton found, NaBH 4 can chemoselectively and stereoselectively reduce the carbonyl group of 2 and leave the oxime group intact, so exo-hydroxyoxime (3) was prepared according to his method.…”

Asymmetric reduction of prochiral ketones with borane using chiral squaric amino alcohols derived from camphor as catalysts

“…The 1,2-amino alcohols 3, 4 from (R)-(+)-camphor were prepared according to the literature procedure [28][29][30]. The squaric acid diesters 2 were formed by refluxing of squaric acid in corresponding alcohols.…”

Enantioselective Synthesis of Chiral Homoallyl Alcohols and Homoallylamines by Nucleophilic Addition of an Allylboron Reagent Modified by a Polymer-Supported Chiral Ligand

“…[13] Reactions were monitored by thin layer chromatography (TLC) using Merck precoated silica gel plates (±)-exo-2-Hydroxy-exo-3-aminobornane was prepared from (1R)-(+)-camphor according to the literature method. [14] A THF solution of 4-vinylbenzenesulfonyl chloride [15] (10 mmol) prepared from sodium 4-vinylbenzene sulfonate was added to a solution of the exo-amino alcohol (1.69 g, 10 mmol) and triethylamine (1.4 mL, 10 mmol) in 50 mL of dry THF. After being stirred for 3 h at room temperature, the reaction mixture was poured into 1 M aqueous HCl at 0°C, and the THF was evaporated under vacuum.…”