75553-23-0Relevant academic research and scientific papers
Ligand-controlled cobalt-catalyzed remote hydroboration and alkene isomerization of allylic siloxanes
Huang, Jiaxin,Li, Jie,Yang, Wen,Zhang, Kezhuo,Zhao, Pei,Zhao, Wanxiang
, p. 302 - 305 (2022/01/03)
The Co-catalyzed remote hydroboration and alkene isomerization of allylic siloxanes were realized by a ligand-controlled strategy. The remote hydroboration with dcype provided borylethers, while xantphos favored the formation of silyl enol ethers.
Stereoselective Carbocyclization of Vinyloxiranes Catalyzed by Lewis Acids: Construction of the Musellarin Tricyclic Core
Yang, Sehui,Park, Euijin,Kim, Jimin
supporting information, p. 667 - 670 (2021/02/05)
Stereoselective carbocyclizations of vinyloxiranes were efficiently catalyzed by Lewis acids to provide cyclic homoallyl alcohols as single isomers. The choice of Lewis acid, B(C6F5)3 was crucial for the stereoselective tr
Iridium-Catalyzed Regioselective Hydroalkynylation of Internal Alkenes Directed by an Oxime
Gao, Peng-Chao,Li, Bi-Jie,Wang, Zi-Xuan
, p. 9500 - 9504 (2021/12/14)
We report here an iridium-catalyzed hydroalkynylation of allylic alcohols protected by an oxime group. Catalytic alkynylation occurs exclusively at the distal position of the alkene. This method generates γ-alkynyl alcohol oximes directly from internal alkenes and terminal alkynes. The oxime group can be readily removed to afford a free alcohol, thus providing an indirect route for the catalytic hydroalkynylation of allylic alcohols.
A Sequential Acyl Thiol-Ene and Thiolactonization Approach for the Synthesis of δ-Thiolactones
McCourt, Ruairí O.,Scanlan, Eoin M.
supporting information, p. 3460 - 3464 (2019/05/10)
A novel strategy for the synthesis of δ-thiolactones from inexpensive and readily available ?-unsaturated esters has been developed. This strategy incorporates a radical acyl thiol-ene reaction as the key C-S bond forming step. Cyclization is achieved via a Steglich-type thiolactonization of 5-mercaptopentanoic acids. We report the facile and scalable synthesis of δ-thiolactones in moderate to good yield under mild reaction conditions with tolerance for a range of functional groups.
Copper-Catalyzed Perfluoroalkylation of Allyl Phosphates with Stable Perfluoroalkylzinc Reagents
Liu, Lihua,Bao, Xifei,Xiao, Hua,Li, Junlan,Ye, Feifan,Wang, Chaoqin,Cai, Qinhua,Fan, Shilu
, p. 423 - 434 (2019/01/08)
A general and practical method for copper-catalyzed cross-coupling of allyl phosphates with stable perfluoroalkylzinc reagents has been developed. The reaction proceeds under mild reaction conditions with high efficiency, good functional group tolerance, and high regio- A nd stereoselectivities and provides general, straightforward, and useful access to allyl-perfluoroalkyl compounds. Preliminary mechanistic studies reveal that the allyl copper intermediate may be involved in the catalytic cycle.
Trifluoromethylation of Unactivated Alkenes with Me3SiCF3 and N-Iodosuccinimide
Yang, Xinkan,Tsui, Gavin Chit
, p. 1521 - 1525 (2019/03/07)
A novel approach to the trifluoromethylation of unactivated alkenes is presented. This reaction is promoted by N-iodosuccinimide (NIS) under visible light irradiation without the need for photocatalysts. The mild conditions allow the direct synthesis of u
Cascade reaction including a formal [5?+?2] cycloaddition by use of alkyne-Co2(CO)6 complex
Sakata, Yuki,Yasui, Eiko,Mizukami, Megumi,Nagumo, Shinji
supporting information, p. 755 - 759 (2019/02/20)
A new cascade reaction including formal [5 + 2] cycloaddition was developed. Treatment of homocinnamyl alcohol and Co2(CO)6-complexed arylpropynal with BF3·OEt2 resulted in the generation of hydrobenzocyclohepta
Acid-catalyzed chirality-transferring intramolecular Friedel-Crafts cyclization of α-hydroxy-α-alkenylsilanes
Sakaguchi, Kazuhiko,Kubota, Shunnichi,Akagi, Wataru,Ikeda, Naoko,Higashino, Masato,Ariyoshi, Shoma,Shinada, Tetsuro,Ohfune, Yasufumi,Nishimura, Takahiro
supporting information, p. 8635 - 8638 (2019/07/25)
Acid-catalyzed intramolecular Friedel-Crafts cyclization of optically active α-hydroxy-α-alkenylsilanes possessing a benzene ring (>99% ee) with TMSOTf as a Lewis acid gave enantio-enriched tetrahydronaphthalenes (up to 98% ee). The silyl group attached to the chiral carbon played a crucial role in the chirality transfer.
Formation of COOH-Ylides, and Their Reactivities and Selectivities in Wittig Reactions
Suganuma, Yuta,Kobayashi, Yuichi
supporting information, p. 333 - 337 (2019/02/12)
Whereas two equivalents of base are typically required to prepare carboxylate (CO 2-) ylides [Ph 3 P + C - (H)-alk-CO 2- ] (alk = alkanediyl) from carboxy (CO 2 H) pho
Stereodivergence in the Ireland-Claisen Rearrangement of α-Alkoxy Esters
Podunavac, Ma?a,Lacharity, Jacob J.,Jones, Kerry E.,Zakarian, Armen
supporting information, p. 4867 - 4870 (2018/08/24)
A systematic investigation into the Ireland-Claisen rearrangement of α-alkoxy esters is reported. In all cases, the use of KN(SiMe3)2 in toluene gave rearrangement products corresponding to a Z-enolate intermediate with excellent diastereoselectivity, presumably because of chelation control. On the other hand, chelation-controlled enolate formation could be overcome for most substrates through the use of lithium diisopropylamide (LDA) in tetrahydrofuran (THF).
