10403-00-6Relevant articles and documents
Copper-catalyzed conjugate addition on macrocyclic, cyclic, and acyclic enones with a chiral phosphoramidite ligand having a C2-symmetric amine moiety
Choi, Yong Hyun,Choi, Jun Young,Yang, Hye Yon,Kim, Yong Hae
, p. 801 - 804 (2002)
A binaphthol-based phosphoramidite ligand (4.2 mol%) having a C2-symmetric chiral amine moiety was examined for enantioselective 1,4-additions of dialkylzinc reagents to various macrocyclic, cyclic, and acyclic enones catalyzed by copper triflate·toluene complex (2 mol%) to afford high enantiomeric excess (up to >95% ee).
Efficient synthesis of (-)-(R)-muscone by enantioselective protonation
Fehr, Charles,Galindo, Jose,Farris, Iris,Cuenca, Ana
, p. 1737 - 1747 (2004)
A new synthesis of (-)-(R)-muscone ((R)-1) by means of enantioselective protonation of a bicyclic ketone enolate as the key step (see 6 → (S)-4 in Scheme 2) is presented. The C15 macrocyclic system is obtained by ozonolysis (Scheme 7).
Ring closing metathesis guided synthesis of (R)-(-)-muscone
Kamat, Vijayendra P.,Hagiwara, Hisahiro,Suzuki, Toshio,Ando, Masayoshi
, p. 2253 - 2254 (1998)
A concise synthesis of the valuable perfumery compound (R)-(-)-muscone 1 in its natural form by making use of the ring closing olefin metathesis (RCM)-aided macrocyclisation route has been achieved.
Cp2ZrMeCl: A Reagent for Asymmetric Methyl Addition
Garrec, Kilian,Fletcher, Stephen P.
, p. 3814 - 3817 (2016)
The use of Cp2ZrMeCl is described as a source of nucleophilic methyl in asymmetric catalysis. This easily prepared reagent is bench stable, weighable in air, and generally useful in highly enantioselective copper-catalyzed addition reactions at room temperature. Methyl is successfully (generally >90% ee) added in 1,4-additions to cyclic and acyclic α,β-unsaturated ketones to provide tertiary and quaternary centers. Examples of catalyst controlled diastereoselective 1,6-addition and dynamic kinetic asymmetric allylic alkylation reactions are also reported. The reagent is used in the catalytic asymmetric synthesis of naturally occurring fragrance (R)-(-)-muscone (82% yield, 91% ee).
Deoxycholic acid-based phosphites as chiral ligands in the enantioselective conjugate addition of dialkylzincs to cyclic enones: Preparation of (-)-(R)-muscone
Iuliano, Anna,Scafato, Patrizia,Torchia, Rita
, p. 2533 - 2538 (2004)
Four phosphites, obtained by linking enantiomerically pure binaphthylchlorophosphite to the two different hydroxy substituted positions of deoxycholic acid, were used as chiral ligands in the enantioselective copper catalysed 1,4-addition of diethylzinc to 2-cyclohexenone and dimethylzinc to 2-cyclopentadecenone. Various reaction parameters were changed in order to select the experimental conditions that would maximise yield and ee. The four ligands were screened for activity and enantioselectivity under the optimised reaction conditions for comparative purposes, in order to establish the influence of the absolute configuration of the binaphthyl moiety as well as the position on the cholestanic backbone of the phosphite moiety. The ligand possessing a (R)-binaphthylphosphite moiety at position 12 of the cholestanic backbone proved to be the most enantioselective affording (-)-(R)-muscone in 63% ee.
Asymmetric conjugate addition of metal alkyl reagents catalyzed by copper complexes with BINPO: A hemilabile P,O-heterobidentate axially chiral ligand
Fuchs, Nicolas,D'Augustin, Magali,Humam, Munir,Alexakis, Alexandre,Taras, Rossana,Gladiali, Serafino
, p. 3143 - 3146 (2005)
We herein report the use of a new class of P,O-bidentate arylphosphine ligand for the asymmetric copper catalyzed conjugate addition of dialkylzinc and trialkylaluminium with the enantiomeric excesses reaching 91% while (R)-muscone was obtained with 77% ee.
Synthesis of (R)-(-)- and (S)-(+)-Muscone of 100percent Optical Purity by Conjugate Addition of Chiral Methylcuprate to (E)-Cyclopentadec-2-enone
Tanaka, Kazuhiko,Suzuki, Hitomi
, p. 101 - 102 (1991)
Synthesis of (R)-(-)- and (S)-(+)-muscone of essentially 100percent enantiomeric excess (e.e.) by the conjugate addition of chiral methylcuprate to (E)-cyclopentadec-2-enone was accomplished by adding small amounts of tetrahydrofuran (THF) as an external ligand to a toluene solution of the chiral methylcuprate.
Synthesis of (R)-(-)-muscone via enzymatic resolution of 3- methylcyclopentadecan-1-ol
Matsumura, Yasufumi,Fukawa, Hidemichi,Terao, Yoshiyasu
, p. 1484 - 1485 (1998)
(R)-(-)-Muscone was synthesized efficiently by oxidation of 3-(R)- methylcyclopentadecan-1-(RS)-ol, which was obtained by lipase-catalyzed resolution of its diastereomeric mixture.
Practical optical resolution of dl-muscone using tartaric acid derivatives as a chiral auxiliary
Takabe, Kunihiko,Sugiura, Masataka,Asumi, Yuya,Mase, Nobuyuki,Yoda, Hidemi,Shimizu, Hiroyasu
, p. 3457 - 3460 (2005)
A simple and practical synthesis of (R)-(-)-muscone was achieved by optical resolution of dl-muscone using tartaric acid derivatives. The acetalization of dl-muscone with N,N′-dibenzyl-l-tartaramide in the presence of Sc(OTf)3 and methyl orthoformate furnished a diastereomeric mixture of acetals, which were readily separated by simple recrystallization. Diastereomerically pure acetal was hydrolyzed to give optically pure muscone and recovered N,N′-dibenzyl-l-tartaramide.
A novel synthetic method for (R)- and (S)-muscones by enantioselective hydrogenation of (E)- and (Z)-3-methyl-2-cyclopentadecen-1-ones catalyzed by p-tolyl-BINAP-Ru(II) complexes
Yamamoto, Takeshi,Ogura, Miharu,Kanisawa, Tsuneyoshi
, p. 9209 - 9212 (2002)
A novel and practical synthesis of (R)- and (S)-muscones by the asymmetric hydrogenation of (E)- and (Z)-3-methyl-2-cyclopentadecen-1-ones catalyzed by p-tolyl-BINAP-Ru(II) complexes has been achieved in nearly complete enantioselectivity.
