70975-26-7Relevant academic research and scientific papers
A Straightforward Sequential Approach for the Enantioselective Synthesis of Optically Active α-Arylmethanol-1,2,3-Triazoles
Andrade, Floyd C. D.,Pugnal, Lucas V. B. L.,Betim, Hugo L. I.,Vani, Jéssica F.,Zukerman-Schpector, Julio,Schwab, Ricardo S.
supporting information, p. 5467 - 5476 (2018/09/14)
Herein we describe a compelling sequential methodology for obtaining optically active α-arylmethanols-1,2,3-triazoles. The approach is based on the enantioselective alkynylation of aldehydes followed by a one-pot two-step desilylation/CuI-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC), providing the corresponding products with excellent yields and high levels of enantioselectivity. Furthermore, the click chemistry can be performed without affecting the enantiomeric excess. The application of the reaction has been demonstrated in the synthesis of a 1,2,3-triazole analog of antihistaminic and anticholinergic drug (R)-orphenadrine.
Lithium binaphtholate-catalyzed asymmetric addition of lithium acetylides to carbonyl compounds
Kotani, Shunsuke,Kukita, Kenji,Tanaka, Kana,Ichibakase, Tomonori,Nakajima, Makoto
, p. 4817 - 4825 (2014/06/23)
The asymmetric addition of lithium acetylides to carbonyl compounds in the presence of a chiral lithium binaphtholate catalyst was developed. A procedure involving the slow addition of carbonyl compounds to lithium acetylides improved the enantioselectivi
Catalytic asymmetric enyne addition to aldehdyes and Rh(I)-catalyzed stereoselective domino Pauson-Khand/[4 + 2] cycloaddition
Chen, Wei,Tay, Jia-Hui,Ying, Jun,Yu, Xiao-Qi,Pu, Lin
, p. 2256 - 2265 (2013/04/24)
The 1,1′-bi-2-naphthol-ZnEt2-Ti(OiPr) 4-Cy2NH system is found to catalyze the 1,3-enyne addition to aliphatic aldehydes as well as other aldehydes at room temperature with 75-96% yield and 82-97% ee. This system is also broadly applicable for the highly enantioselective reaction of other alkyl-, aryl-, and silylalkynes with structurally diverse aldehydes. The propargylic alcohols prepared from the catalytic asymmetric enyne addition to aliphatic aldehydes are used to prepare a series of optically active trienynes. In the presence of a catalytic amount of [RhCl(CO)2]2 and 1 atm of CO, the optically active trienynes undergo highly stereoselective domino Pauson-Khand/[4 + 2] cycloaddition to generate optically active multicyclic products. The Rh(I) catalyst is also found to catalyze the coupling of a diyne with CO followed by [4 + 2] cycloaddition to generate an optically active multicyclic product. These transformations are potentially useful for the asymmetric synthesis of polyquinanes containing a quaternary chiral carbon center.
Gold-catalyzed regioselective hydration of propargyl acetates assisted by a neighboring carbonyl group: Access to α-acyloxy methyl ketones and synthesis of (±)-actinopolymorphol B
Ghosh, Nayan,Nayak, Sanatan,Sahoo, Akhila K.
supporting information; experimental part, p. 500 - 511 (2011/04/17)
A general atom-economical approach for the synthesis of α-acyloxy methyl ketone is demonstrated through regioselective hydration of a wide range of propargyl acetates. Readily available catalyst comprising of 1% Ph 3PAuCl and 1% AgSbF6 in dioxane-H2O efficiently hydrolyzes the terminal alkynes of the propargyl acetate in the absence of acid promoters at ambient temperature within a short time. Effective regioselective hydration is facilitated by the neighboring carbonyl group as demonstrated through 18O-labeling study. Compatibility of functional moieties and tolerance to various acid-labile protecting groups are observed. The catalytic condition is also suitable to perform hydration of TMS-substituted propargyl acetates, even though it requires prolonged reaction time for completion. Stereointegrity of the propargylic acetate is preserved during the hydration. The robustness of the system is successfully demonstrated through gram scale preparation of the product in nearly quantitative yield. The common α-acyloxy methyl ketone is transformed to 1,2-diol and 1,2-amino alcohol derivatives. Synthesis of actinopolymorphol B is achieved for the first time involving hydration of the propargyl acetate as the key step.
Highly enantioselective addition of trimethylsilylacetylene to aldehydes catalyzed by a zinc-amino-alcohol complex
Li, Zhi-Yuan,Wang, Min,Bian, Qing-Hua,Zheng, Bing,Mao, Jian-You,Li, Shuo-Ning,Liu, Shang-Zhong,Wang, Ming-An,Zhong, Jiang-Chun,Guo, Hong-Chao
supporting information; experimental part, p. 5782 - 5786 (2011/06/26)
A fine addition! A highly enantioselective and efficient procedure for the amino-alcohol-zinc-catalyzed addition of trimethylsilylacetylene to aromatic, α,β-unsaturated, and aliphatic aldehydes has been developed (see scheme; R=aryl, alkynyl, or alkyl; TMS=trimethylsilyl; TBDMS=tert- butyldimethylsilyl). The present protocol was successfully applied in the concise synthesis of the natural products marine alkynol and falcarindiol. Copyright
Asymmetric direct alkynylation catalyzed by chiral ru-bis(oxazolinyl)phenyl complexes
Ito, Jun-Ichi,Asai, Ryosuke,Nishiyama, Hisao
supporting information; experimental part, p. 3860 - 3862 (2010/11/17)
Propargylic alcohols were obtained with excellent enantioselectivities in the asymmetric direct alkynylation of aldehydes using 5 mol % of chiral ruthenium complexes containing the chiral bis(oxazolinyl)phenyl ligand.
l-Proline-derived tertiary amino alcohol as a new chiral ligand for enantioselective alkynylation of aldehydes
Xu, Zhou,Wu, Nan,Ding, Zhenhua,Wang, Ting,Mao, Jincheng,Zhang, Yawen
scheme or table, p. 926 - 929 (2009/05/11)
The easily prepared chiral tertiary amino alcohol 1a was found to catalyze the reaction of alkynylzinc reagents with various aldehydes to generate chiral propargylic alcohols with moderate-to-good enantioselectivities. The mechanism of the reaction is als
Amino thiols versus amino alcohols in the asymmetric alkynylzinc addition to aldehydes
Subirats, Silvia,Jimeno, Ciril,Pericas, Miquel A.
experimental part, p. 1413 - 1418 (2009/12/03)
A series of modular amino thiol and amino alcohol ligands have been synthesized in enantiopure form from common enantiopure precursors. Their structures have been optimized for performance in the asymmetric alkynylzinc addition to aldehydes, and a direct
Catalytic enantioselective addition of terminal alkynes to aromatic aldehydes using zinc-hydroxyamide complexes
Blay, Gonzalo,Cardona, Luz,Fernandez, Isabel,Marco-Aleixandre, Alicia,Munoz, M. Carmen,Pedro, Jose R.
experimental part, p. 4301 - 4308 (2009/12/05)
A mandelamide ligand, derived from (S)-mandelic acid and (S)-phenylethanamine, catalyzes the addition of aryl-, alkyl- and silyl-alkynylzinc reagents to aromatic and heteroaromatic aldehydes with good yields and good to high enantioselectivities.
Facile, mild, and highly enantioselective alkynylzinc addition to aromatic aldehydes by BINOL/N-methylimidazole dual catalysis
Yang, Fei,Xi, Peihua,Yang, Li,Lan, Jingbo,Xie, Rugang,You, Jingsong
, p. 5457 - 5460 (2008/02/08)
(Chemical Equation Presented) The dual Lewis acid/base catalytic system, generated from N-methylimidazole (NMI), (R)-1,1′-bi-2-naphthol [(R)-BINOL], and Ti(OiPr)4, effectively catalyzes the enantioselective alkynylation of aldehydes in the pres
