151379-71-4Relevant academic research and scientific papers
Asymmetric Synthesis of (R)-(-)- and (S)-(+)-Muscone by Enantioselective Conjugate Addition of Chiral Dimethylcuprate to (E)-Cyclopentadec-2-en-1-one
Tanaka, Kazuhiko,Ushio, Hideki,Kawabata, Yasuyuki,Suzuki, Hitomi
, p. 1445 - 1452 (1991)
A variety of optically active secondary amino alcohols have been prepared from camphor and screened as chiral non-transferable cuprate ligands in conjugate addition reactions.The reactions of (E)-cyclopentadec-2-en-1-one with chiral dimethylcuprates derived from the ligand in toluene afforded muscone in enantiomeric excesses as high as 26 - 89 percent.The stereochemistry of the product correlates with the configuration of the chiral ligand used.Thus the conjugate addition using the ligand prepared from exo-3-monosubstituted-amino-exo-2-hydroxybornane gave (S)-(+)-muscone, while with endo-ligand, (R)-(-)-muscone was obtained in higher enantioselectivity.Muscone of essentially 100percent optical purity was obtained by the addition of small amounts of THF (tetrahydrofuran) (2 - 10 equiv.) to the toluene solution of the chiral cuprate reagent prepared from (1R,2R,3S,4S)-3--1,7,7-trimethylbicycloheptan-2-ol 23 (endo-MPATH).The effect of the stoichiometry of the chiral ligand and the cuprate reagent on the chemical yield and enantioselectivity was briefly investigated.
Preparative scale synthesis of (+) endo-2-hydroxy-endo-3-aminobornane
M'Boungou-M'Passi, A.,Henin, F.,Muzart, J.,Pete, J. P.
, p. 214 - 217 (2007/10/02)
A convenient preparation of the enantiomerically pure title compound is proposed from (+) camphor in 5 steps with an overall yield between 42 and 62percent.The benzoylation of this compound leads to the expected products 6 and 8 and to the oxazoline 10 formed from 6 with retention of configuration.Key Words: chiral 2-hydroxy-3-aminobornanes / benzoylation / acidic hydrolysis
