960377-64-4Relevant academic research and scientific papers
Trialkylborane-Mediated Propargylation of Aldehydes Using γ-Stannylated Propargyl Acetates
Horino, Yoshikazu,Murakami, Miki,Ishibashi, Mayo,Lee, Jun Hee,Watanabe, Airi,Matsumoto, Rio,Abe, Hitoshi
supporting information, p. 9564 - 9568 (2019/12/24)
A transition-metal-free three-component process that combines aldehydes, 3-(tributylstannyl)propargyl acetates formed in situ from readily available propargyl acetates, and trialkylboranes provides access to a range of 1,2,4-trisubstituted homopropargylic alcohols. The addition of diisopropylamine plays a crucial role in the selective formation of homopropargylic alcohols. Importantly, this methodology can be extended to a single-flask reaction sequence starting from propargyl acetates.
Diastereo- and enantioselective propargylation of benzofuranones catalyzed by pybox-copper complex
Zhao, Long,Huang, Guanxin,Guo, Beibei,Xu, Lijun,Chen, Jie,Cao, Weiguo,Zhao, Gang,Wu, Xiaoyu
supporting information, p. 5584 - 5587 (2015/02/19)
Diastereo- and enantioselective preparation of 2,2-disubstituted benzofuran-3(2H)-one has been realized by a pybox-copper catalyzed reaction between 2-substituted benzofuran-3(2H)-one and propargyl acetate. The utility of this method was demonstrated by further transformation of the terminal alkyne into a methyl ketone without loss of enantiomeric purity.
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.
Asymmetrie copper-catalyzed propargylic substitution reaction of propargylic acetates with enamines
Fang, Ping,Hou, Xue-Long
supporting information; experimental part, p. 4612 - 4615 (2009/12/09)
Enamines served as carbon-nucleophiles for the first time In the Cu-catalyzed asymmetric propargylic substitution reaction of propargylic acetates, providing corresponding chiral β-ethynyl-substituted ketones In high yields and In good to high enantioselectivity.
Copper-catalyzed asymmetric propargylic substitution reactions of propargylic acetates with amines
Hattori, Gaku,Matsuzawa, Hiroshi,Miyake, Yoshihiro,Nishibayashi, Yoshiaki
supporting information; experimental part, p. 3781 - 3783 (2009/02/07)
(Chemical Equation Presented) Flexing your bipheps: Enantioselective propargylic substitution reactions of propargylic acetates with amines catalyzed by a copper-(R)-Cl-MeO-biphep or -binap complex give the corresponding propargylic amines in excellent yi
