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).
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).
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)-(-)-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.
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.
Asymmetric Synthesis of (R)-Muscone by Enantioselective Addition of Chiral Methyl Cuprate to (E)-2-Cyclopentadecen-1-one
Tanaka, Kazuhiko,Ushio, Hideki,Suzuki, Hitomi
, p. 795 - 797 (1990)
(R)-(-)-Muscone was prepared in 89percent enantiomeric excess using newly devised chiral ligands such as (1R,2R,3S,4S)-3--1,7,7-trimethylbicycloheptan-2-ol in conjugate addition of methyl cuprate to (E)-2-cyclopentadecen-1-one.
Asymmetric activation of tropos catalysts in the stereoselective catalytic conjugate additions of R2Zn to α,β-enones: An efficient synthesis of (-)-muscone
Scafato, Patrizia,Cunsolo, Giovanni,Labano, Stefania,Rosini, Carlo
, p. 8801 - 8806 (2004)
The preparation of a new phosphoramidite starting from (R)-BINOL and a biphenylamine is presented. In such a compound the chirality is due only to atropisomerism and this molecule possesses a flexible biphenylamine residue. Therefore it can work as a tropos catalyst. The catalytic efficiency of this new phosphoramidite has been tested in some asymmetric conjugate additions of dialkylzinc reagents to α,β-enones and compared with that of an analogous already known non-tropos ligand. Interestingly, while comparable results were obtained in the addition of ZnEt2 to chalcone and cyclohexenone, in the case of the addition of ZnMe2 to (E)-cyclopentadec-2-en-1-one, the new ligand provides (-)-muscone, a valuable ingredient of the perfume industry, in 84% ee, while the non-tropos ligand gives a much lower (57%) ee value. Graphical Abstract
Method for preparing L-muscone
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, (2020/04/02)
The invention discloses a method for preparing L-muscone. The method comprises the following steps: (1) L-muscone in racemic muscone and a chiral hydroxybenzene compound generate L-enantiomer salt under laser irradiation; and (2) crystallization separation and hydrolysis are performed on the L-enantiomer salt to obtain a L-muscone product, wherein the step (1) is carried out in the presence of a Bronsted acid catalyst. Preferably, after hydrolysis in the step (2), separation, purification and other steps are carried out to obtain the L-muscone product. The raw material used in the method is the racemic muscone with a mature production process; batch production can be realized, diastereomer salifying resolution is carried out by adopting laser irradiation, the product selectivity is greatlyimproved, the method is green, pollution-free, and less in production of three wastes, the chiral hydroxybenzene compound is convenient to recover and reusable, the atom economy is high, the productselectivity is high, and the method is suitable for being used in the fields of biology, medical treatment, medicines, spices, cosmetics and the like.
(E)-3-METHYL-2-CYCLOALKENONE COMPOUND, 3-HALO-3-METHYLCYCLOALKANONE COMPOUND AND METHOD FOR PRODUCING (R)-3-METHYLCYCLOALKANONE COMPOUND
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Paragraph 0268-0271; 0290; 0291, (2018/06/29)
PROBLEM TO BE SOLVED: To provide novel (E)-3-methyl-2-cycloalkenone compounds and 3-halo-3-methylcycloalkanone compounds, and also provide a production method that can efficiently produce (R)-3-methylcycloalkanone compounds. SOLUTION: An (E)-3-methyl-2-cycloalkenone compound has a chemical structure represented by the following formula (1) (where n is an integer of 1-5, 7 or 8). SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
