104281-52-9Relevant articles and documents
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 (2007/10/02)
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.
REARRANGEMENT OF CYCLIC ALCOHOLS WITH AN ADJACENT PHENYLTHIO (PhS-) GROUP: MIGRATION OF A PhS GROUP AROUND A RING.
Hannaby, Malcolm,Warren, Stuart
, p. 765 - 768 (2007/10/02)
PhS migratoin around rings (size 5-15) gives allyl sulphides with a regioselectivity wich varies with ring size.
