- Compound with cinnamon fragrance as well as preparation method and application thereof
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The invention relates to a compound with cinnamon fragrance as well as a preparation method and application thereof. The compound has the following structural formula, wherein the structural formula can be named as 2-decenoic acid-2-(4-methoxy)-phenyl-2-butyl ester. The provided compound has the advantages of obvious cinnamon aroma, rich aroma, lasting aroma and good stability, and enriches the sources of cinnamon aroma. When the essence is prepared in different periods, the compound has consistent cinnamon aroma, so that the required aroma can be accurately mastered.
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- Harnessing the Power of the Asymmetric Grignard Synthesis of Tertiary Alcohols: Ligand Development and Improved Scope Exemplified by One-Step Gossonorol Synthesis
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A series of N-substituted cyclohexyldiaminophenolic ligands for the asymmetric Grignard synthesis of tertiary alcohols is reported. The 2,5-dimethylpyrrole-decorated ligand led to improved enantioselectivities and broadened the scope of the methodology. As an exemplar, we report an unprecedented highly selective one-step synthesis of gossonorol in 93% ee, also constituting the shortest formal syntheses of natural products boivinianin B and yingzhaosu C.
- Gilheany, Declan G.,Kavanagh, Saranna E.
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supporting information
p. 8198 - 8203
(2020/11/18)
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- Enantioselective α-arylation of O-carbamates via sparteine-mediated lithiation and Negishi cross-coupling
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A general and highly enantioselective arylation of carbamates derived from primary alcohols was developed by combining Hoppe's sparteine-mediated asymmetric lithiation with Negishi cross-coupling. Coupled with Aggarwal's lithiation-borylation sequence, the current method provides a short and divergent access to a variety of enantioenriched secondary and tertiary benzylic alcohols.
- Royal, Titouan,Baumgartner, Yann,Baudoin, Olivier
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supporting information
p. 166 - 169
(2017/11/27)
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- Asymmetric Grignard Synthesis of Tertiary Alcohols through Rational Ligand Design
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A simple, general and practical method is reported for highly enantioselective construction of tertiary alcohols through the direct addition of organomagnesium reagents to ketones. Discovered by rational ligand design based on a mechanistic hypothesis, it has an unprecedented broad scope. It utilizes a new type of chiral tridentate diamine/phenol ligand that is easily removed from the reaction mixture. It is exemplified by application to a formal asymmetric synthesis (>95:5 d.r.) of vitamin E.
- Bieszczad, Bartosz,Gilheany, Declan G.
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supporting information
p. 4272 - 4276
(2017/04/03)
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- CHIRAL DIAMINE COMPOUNDS FOR THE PREPARATION OF CHIRAL ALCOHOL AND CHIRAL AMINE
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A process for the stereoselective preparation of a chiral alcohol or a chiral amine, the process comprising reacting a first prochiral reactant selected from the group consisting of a ketone, an aldehyde, and an inline, with a second reactant comprising a Grignard reagent, in the presence of a chiral trans-diamim of formula (1) as defined herein. Also provided is the use of the chiral trans-diamine of formula (1) in a Grignard reaction and the chiral trans-diamines per se.
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Page/Page column 45; 46
(2015/12/17)
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- Commercially available neat organozincs as highly reactive reagents for catalytic enantioselective addition to ketones and aldehydes under solvent free conditions
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Neat Et2Zn, Ph2Zn, and highly concentrated Me 2Zn are highly reactive organozinc reagents, which are commercially available in bulk quantities. We here report a catalytic enantioselective Et2Zn, Ph2Zn, and Me2Zn addition to ketones and aldehydes under solvent free or highly concentrated conditions without Ti(Oi-Pr)4 as a conventional activator of organozinc reagents. The desired optically active tertiary and secondary alcohols were obtained in good yield with high enantioselectivity when compared to the conventional solvent-use conditions. From the viewpoint of ecological and environmental reasons in green chemistry, this catalysis would be practical for not only academic but also industrial use.
- Hatano, Manabu,Mizuno, Tomokazu,Ishihara, Kazuaki
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experimental part
p. 4417 - 4424
(2011/08/06)
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- Improved method for the conversion of pinacolboronic esters into trifluoroborate salts: facile synthesis of chiral secondary and tertiary trifluoroborates
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A general method for the preparation of virtually any potassium trifluoroborate salt from the corresponding pinacolboronic ester is reported. Thus, conditions for an azeotropic removal of pinacol from the reaction mixture were found to afford the desired potassium trifluoroborates of sufficient purity (>95%) in nearly quantitative yields irrespective of the nature of the product. The utility of this method is illustrated by the preparation of a broad range of enantioenriched secondary and tertiary potassium trifluoroborates.
- Bagutski, Viktor,Ros, Abel,Aggarwal, Varinder K.
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supporting information; experimental part
p. 9956 - 9960
(2010/02/27)
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- A green chemistry approach to a more efficient asymmetric catalyst: Solvent-free and highly concentrated alkyl additions to ketones
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There is a great demand for development of catalyst systems that are not only efficient and highly enantioselective but are also environmentally benign. Herein we report investigations into the catalytic asymmetric addition of alkyl and functionalized alk
- Jeon, Sang-Jin,Li, Hongmei,Walsh, Patrick J.
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p. 16416 - 16425
(2007/10/03)
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- Catalytic asymmetric addition of alkylzinc and functionalized alkylzinc reagents to ketones
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(Chemical Equation Presented) We describe our full report of the catalytic asymmetric addition of simple and functionalized dialkylzinc reagents to a broad range of saturated ketones and enones. The functionalized organozinc reagents contain esters, silyl
- Jeon, Sang-Jin,Li, Hongmei,Garcia, Celina,LaRochelle, Lynne K.,Walsh, Patrick J.
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p. 448 - 455
(2007/10/03)
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- A practical catalytic asymmetric addition of alkyl groups to ketones
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Many catalysts will promote the asymmetric addition of alkylzinc reagents to aldehydes. In contrast, there are no reports of additions to ketones that are both general and highly enantioselective. We describe herein a practical catalytic asymmetric additi
- Garcia, Celina,LaRochelle, Lynne K.,Walsh, Patrick J.
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p. 10970 - 10971
(2007/10/03)
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- Vilsmeier-Haack reaction of tertiary alcohols: Formation of functionalised pyridines and naphthyridines
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Vilsmeier-Haack reaction of 2-arylpropan-2-ols proceeds with multiple iminoalkylations leading to the formation of conjugated iminium salts which on ammonium acetate-induced cyclisation afford 4-arylnicotinaldehydes in good yields. Tertiary alcohols derived from aliphatic or alicyclic ketones by the addition of methyl Grignard are converted into substituted pyridines and naphthyridines by the action of Vilsmeier's reagent in N,N-dimethylformamide followed by nucleophile-assisted cyclisation in the presence of ammonium acetate.
- Thomas,Asokan
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p. 2583 - 2587
(2007/10/03)
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- Electrochemical alkyl transfer reactions of trialkylborane to carbonyl compounds by use of copper sacrificial anode
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Alkyl groups in trialkylboranes were successfully transferred to carbonyl compounds in the presence of the platinum cathode and copper anode by electrochemical method. The new, mild electrochemical alkyl transfer reaction produced various substituted alcohols in good yields.
- Choi, Jung Hoon,Youm, Jong Sung,Cho, Cheon-Gyu,Czae, Myung-Zoon,Hwang, Book Kee,Kim, Jung Sung
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p. 4835 - 4838
(2007/10/03)
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- Highly enantioselective addition of primary alkyl Grignard reagents to carbocyclic and heterocyclic arylketones in the presence of magnesium TADDOLate preparative and mechanistic aspects
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In the presence of equimolar amounts of the Mg alkoxide from α,α,α',α'-tetraphenyl-2,2-dimethyl-1,3-dioxolan-4,5-dimethanol (a TADDOL) primary Grignard reagents (Et, Pr, Bu, Oct, 3-butenyl) add to carbo- and heteroaromatic methyl ketones in THF at -100°C to give tertiary alcohols of enantiomeric excesses reaching values above 98%. The scope and limitation of the method are investigated. The reaction, which occurs in a vigorously stirred heterogeneous mixture, give best results in the absence of steric hindrance of the reacting centers; Grignard reagents made from alkyl bromides are superior to those obtained from chlorides; there is a perfect linear relationship between the ee of the TADDOL and of the product 2-phenyl-2-decanol; those tertiary alcohols of which the absolute configuration is known, are formed by nucleophilic attack from the Re face of the keto carbonyl groups. Three tentative mechanistic models for the stereochemical course of the reaction are discussed.
- Weber, Beat,Seebach, Dieter
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p. 6117 - 6128
(2007/10/02)
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- The Importance of Resonance Stabilization in the Benzylic Solvolysis. Substituent Effects on the Solvolysis of α,α-Diisopropylbenzyl Chlorides
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The substituent effect on the solvolysis of α,α-diisopropylbenzyl chlorides can be described in terms of ?+ value.No significant steric loss of resonance was observed by introducing two bulky isopropyl groups into benzylic reaction center.
- Fujio, Mizue,Nakata, Kazuhide,Kuwamura, Takashi,Nakamura, Hirotaka,Saeki, Yoshihiro,et al.
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p. 8309 - 8312
(2007/10/02)
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- The Synthesis of Hydroxyphenylthiophenes
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The synthesis of the five isomeric methoxyphenylthiophenes is described.The methoxy compounds were hydrolyzed to yield the hydroxyphenylthiophenes.
- Baldwin, Larry J.,Pakray, Sudabeh,Castle, Raymond N.,Lee, Milton L.
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p. 1667 - 1669
(2007/10/02)
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- Antiestrogens. Synthesis and Evaluation of Mammary Tumor Inhibiting Activity of 1,1,2,2-Tetraalkyl-1,2-diphenylethanes
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Among the newly synthesized 1,1,2,2-tetraalkyl-1,2-diphenylethanes, 1,1,2,2-tetramethyl-1,2-bis(4'-hydroxyphenyl)ethane (23) and 1,1,2,2-tetramethyl-1,2-bis(3'-hydroxyphenyl)ethane (26) were the most active compounds regarding estradiol receptor affinity, exhibiting Ka values of 0.73*108 and 0.67*108 M-1, respectively.In vivo, 23 and 26 showed only very small uterotrophic activity in the mouse.They strongly inhibited (73percent) the estrone-stimulated mouse uterine growth.Tested on the 9,10-dimethyl-1,2-benzanthracene induced hormone-dependent mammary adenocarcinoma of the Sprague-Dawley rat, compounds 23 and 26 exhibited a dose-dependent inhibition of the tumor growth, having a strong effect at a dose of 20 (mg/kg)/day (compound 23).
- Hartmann, Rolf W.,Kranzfelder, Gerhard,Angerer, Erwin, v.,Schoenenberger, Helmut
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p. 841 - 848
(2007/10/02)
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