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Asymmetric Synthesis of (R)-(-)- and (S)-(+)-Muscone by Enantioselective Conjugate Addition of Chiral Dimethylcuprate to (E)-Cyclopentadec-2-en-1-one

DOI: 10.1039/P19910001445

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1445 - 1452 (1991)

Update date:2022-08-05

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Authors:

Tanaka, KazuhikoTanaka, Kazuhiko

Ushio, HidekiUshio, Hideki

Kawabata, YasuyukiKawabata, Yasuyuki

Suzuki, HitomiSuzuki, Hitomi

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Article abstract of DOI:10.1039/P19910001445

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-methylpyrrol-2-yl)methylamino>-1,7,7-trimethylbicyclo<2.2.1>heptan-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.

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Product name:(1R,2S,3S,4S)-3-benzoylamino-1,7,7-trimethylbicyclo<2.2.1>heptan-2-ol

Cas No:151379-71-4

151379-71-4

R&D Labs maybe for 151379-71-4

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