30068-21-4Relevant academic research and scientific papers
Compound with cinnamon fragrance as well as preparation method and application thereof
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Paragraph 0104; 0109-0111; 0126; 0130-0131; 0137-0138; 0141, (2021/04/10)
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.
Harnessing the Power of the Asymmetric Grignard Synthesis of Tertiary Alcohols: Ligand Development and Improved Scope Exemplified by One-Step Gossonorol Synthesis
Gilheany, Declan G.,Kavanagh, Saranna E.
supporting information, p. 8198 - 8203 (2020/11/18)
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.
Enantioselective α-arylation of O-carbamates via sparteine-mediated lithiation and Negishi cross-coupling
Royal, Titouan,Baumgartner, Yann,Baudoin, Olivier
supporting information, p. 166 - 169 (2017/11/27)
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.
Asymmetric Grignard Synthesis of Tertiary Alcohols through Rational Ligand Design
Bieszczad, Bartosz,Gilheany, Declan G.
supporting information, p. 4272 - 4276 (2017/04/03)
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.
CHIRAL DIAMINE COMPOUNDS FOR THE PREPARATION OF CHIRAL ALCOHOL AND CHIRAL AMINE
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Page/Page column 45; 46, (2015/12/17)
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.
Commercially available neat organozincs as highly reactive reagents for catalytic enantioselective addition to ketones and aldehydes under solvent free conditions
Hatano, Manabu,Mizuno, Tomokazu,Ishihara, Kazuaki
experimental part, p. 4417 - 4424 (2011/08/06)
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.
Improved method for the conversion of pinacolboronic esters into trifluoroborate salts: facile synthesis of chiral secondary and tertiary trifluoroborates
Bagutski, Viktor,Ros, Abel,Aggarwal, Varinder K.
supporting information; experimental part, p. 9956 - 9960 (2010/02/27)
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.
A green chemistry approach to a more efficient asymmetric catalyst: Solvent-free and highly concentrated alkyl additions to ketones
Jeon, Sang-Jin,Li, Hongmei,Walsh, Patrick J.
, p. 16416 - 16425 (2007/10/03)
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
Catalytic asymmetric addition of alkylzinc and functionalized alkylzinc reagents to ketones
Jeon, Sang-Jin,Li, Hongmei,Garcia, Celina,LaRochelle, Lynne K.,Walsh, Patrick J.
, p. 448 - 455 (2007/10/03)
(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
A practical catalytic asymmetric addition of alkyl groups to ketones
Garcia, Celina,LaRochelle, Lynne K.,Walsh, Patrick J.
, p. 10970 - 10971 (2007/10/03)
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
