93404-35-4Relevant academic research and scientific papers
DMAP-Catalyzed [4 + 2] Cycloaddition of α,β-Unsaturated Carboxylic Acids with Ketones for Synthesis of α,β-Unsaturated δ-Lactones
Jin, Jinghai,Xu, Qinchang,Deng, Weiping
supporting information, p. 397 - 400 (2017/04/27)
The DMAP-catalyzed [4 + 2] cycloaddition of α,β-unsaturated carboxylic acids with ketones furnishing α,β-unsaturated δ-lactones in good yields (up to 80%) is described, which is the first example of remote γ-C(sp3)-H activation of α,β-unsaturated carboxylic acids facilitated by DMAP, a pyridine-based catalyst. Copyright
Highly efficient synthesis of chiral aromatic ketones: Via Rh-catalyzed asymmetric hydrogenation of β,β-disubstituted enones
Zhang, Tao,Jiang, Jun,Yao, Lin,Geng, Huiling,Zhang, Xumu
supporting information, p. 9258 - 9261 (2017/08/22)
A succinct and efficient protocol was developed for the synthesis of chiral aromatic ketones via asymmetric hydrogenation of β,β-disubstituted enones with rhodium catalysts based on chiral bisphosphine thiourea ligands. A series of substrates (17 examples) was smoothly catalyzed to afford the corresponding chiral aromatic ketones in high conversions (>99%) with excellent enantioselectivities (up to 96% ee).
Rhodium-Catalyzed Asymmetric Hydrogenation of α,β-Unsaturated Carbonyl Compounds via Thiourea Hydrogen Bonding
Wen, Jialin,Jiang, Jun,Zhang, Xumu
supporting information, p. 4451 - 4453 (2016/09/28)
The strategy of secondary interaction enables enantioselectivity for homogeneous hydrogenation. By introducing hydrogen bonding of substrates with thiourea from the ligand, α,β-unsaturated carbonyl compounds, such as amides and esters, are hydrogenated wi
Enantioselective Rh-catalyzed hydrogenation of 3-aryl-4-phosphonobutenoates with a P-stereogenic BoPhoz-type ligand
Duan, Zheng-Chao,Hu, Xiang-Ping,Zhang, Cheng,Zheng, Zhuo
supporting information; experimental part, p. 8319 - 8321 (2011/03/17)
A series of chiral 3-aryl-4-phosphonobutyric acid esters were synthesized in high enantioselectivities (93-98% ee) via the Rh-catalyzed asymmetric hydrogenation of the corresponding 3-aryl-4-phosphonobutenoates using a P-stereogenic BoPhoz-type phosphine-aminophosphine ligand. The methodology has been successfully applied to the asymmetric synthesis of a potential GABA B antagonist, (R)-phaclofen, in high enantioselectivity.
General, robust, and stereocomplementary preparation of β-ketoester enol tosylates as cross-coupling partners utilizing TsCl-N-methylimidazole agents
Nakatsuji, Hidefumi,Ueno, Kanako,Misaki, Tomonori,Tanabe, Yoo
supporting information; scheme or table, p. 2131 - 2134 (2009/05/26)
(Chemical Equation Presented) We have developed a general, robust, and cost-effective method for the (E)- or (Z)-stereocomplementary enol tosylation of β-ketoesters using TsCl-N-methylimidazole (NMI)-Et3N or LiOH. TsCl coupled with NMI formed a
Polarized Ketene Dithioacetals. Part 42. Studies on the Reactions of Alkyl and Aryl Grignard Reagents with α-Oxoketene Dithioacetals
Singh, Gurdeep,Purkayastha, Makhan L.,Ila, Hiriyakkanavar,Junjappa, Hiriyakkanavar
, p. 1289 - 1294 (2007/10/02)
The oxoketene dithioacetals (2a-k) derived from a variety of cyclic and acyclic active methylene ketones undergo 1,2-addition with methylmagnesium iodide to give the alcohol acetals (3a-k) which, on subsequent boron trifluoride-ether catalysed methanolysi
(Z)‐enol p‐tosylate derived from methyl acetoacetate: A useful cross‐coupling partner for the synthesis of methyl (Z)‐3‐phenyl (or aryl)‐2‐butenoate
Ashida, Yuichiro,Nakatsuji, Hidefumi,Tanabe, Yoo
, (2018/11/25)
Procedures yielding (Z)‐3‐(p‐toluenesulfonyloxy)but‐2‐enoate [(Z)‐1] as white prisms and methyl (Z)‐3‐phenyl‐2‐butenoate [(Z)‐2] as a colorless oil are presented. Following are notes on the instruments and chemicals used and required. The chapter conclude
