- A New Strategy for Enantioselective Construction of Multisubstituted Five-Membered Oxygen Heterocycles via a Domino Michael/Hemiketalization Reaction
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A new highly enantioselective domino Michael/hemiketalization reaction of α-hydroxyacetophenone with β,γ-unsaturated α-keto esters for the synthesis of 2,2,4,5-tetrasubstituted chiral tetrahydrofurans is reported. With 2 mol% intramolecular dinuclear zinc
- Hua, Yuan-Zhao,Liu, Meng-Meng,Huang, Pei-Jin,Song, Xixi,Wang, Min-Can,Chang, Jun-Biao
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- Diversity-Oriented Synthesis of Spirocyclohexene Indane-1,3-diones and Coumarin-Fused Cyclopentanes via an Organobase-Controlled Cascade Reaction
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An organobase-controlled, divergent cascade reaction to construct spirocyclohexene indane-1,3-diones and coumarin-fused cyclopentanes is reported. The cascade reaction is triggered by the 1,6-addition of 3-homoacylcoumarins to the indanedione-derived acce
- Wang, Min,Tseng, Ping-Yao,Chi, Woei-Jye,Suresh, Sundaram,Edukondalu, Athukuri,Chen, Yi-Ru,Lin, Wenwei
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supporting information
p. 3407 - 3415
(2020/07/16)
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- Asymmetric Catalytic Formal 1,4-Allylation of β,γ-Unsaturated α-Ketoesters: Allylboration/Oxy-Cope Rearrangement
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A highly enantioselective formal conjugate allyl addition of allylboronic acids to β,γ-unsaturated α-ketoesters has been realized by employing a chiral NiII/N,N′-dioxide complex as the catalyst. This transformation proceeds by an allylboration/oxy-Cope rearrangement sequence, providing a facile and rapid route to γ-allyl-α-ketoesters with moderate to good yields (65–92 %) and excellent ee values (90–99 % ee). The isolation of 1,2-allylboration products provided insight into the mechanism of the subsequent oxy-Cope rearrangement reaction: substrate-induced chiral transfer and a chiral Lewis acid accelerated process. Based on the experimental investigations and DFT calculations, a rare boatlike transition-state model is proposed as the origin of high chirality transfer during the oxy-Cope rearrangement.
- Tang, Qiong,Fu, Kai,Ruan, Peiran,Dong, Shunxi,Su, Zhishan,Liu, Xiaohua,Feng, Xiaoming
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supporting information
p. 11846 - 11851
(2019/07/19)
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- Photoactivity hexahydroquinolinone and preparation method thereof
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The invention discloses photoactivity hexahydroquinolinone and a preparation method thereof. The photoactivity hexahydroquinolinone is a diastereoisomer consisting of a compound shown as a formula I and a compound shown as a formula II, wherein a diastere
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Paragraph 0051; 0133-0135
(2017/07/21)
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- Boosting Chemical Stability, Catalytic Activity, and Enantioselectivity of Metal-Organic Frameworks for Batch and Flow Reactions
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A key challenge in heterogeneous catalysis is the design and synthesis of heterogeneous catalysts featuring high catalytic activity, selectivity, and recyclability. Here we demonstrate that high-performance heterogeneous asymmetric catalysts can be engineered from a metal-organic framework (MOF) platform by using a ligand design strategy. Three porous chiral MOFs with the framework formula [Mn2L(H2O)2] are prepared from enantiopure phosphono-carboxylate ligands of 1,1′-biphenol that are functionalized with 3,5-bis(trifluoromethyl)-, bismethyl-, and bisfluoro-phenyl substituents at the 3,3′-position. For the first time, we show that not only chemical stability but also catalytic activity and stereoselectivity of the MOFs can be tuned by modifying the ligand structures. Particularly, the MOF incorporated with -CF3 groups on the pore walls exhibits enhanced tolerance to water, weak acid, and base compared with the MOFs with -F and -Me groups. Under both batch and flow reaction systems, the CF3-containing MOF demonstrated excellent reactivity, selectivity, and recyclability, affording high yields and enantioselectivities for alkylations of indoles and pyrrole with a range of ketoesters or nitroalkenes. In contrast, the corresponding homogeneous catalysts gave low enantioselectivity in catalyzing the tested reactions.
- Chen, Xu,Jiang, Hong,Hou, Bang,Gong, Wei,Liu, Yan,Cui, Yong
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supporting information
p. 13476 - 13482
(2017/10/05)
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- GLUCOSYLCERAMIDE SYNTHASE INHIBITORS FOR THE TREATMENT OF DISEASES
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Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions associated with the enzyme glucosylceramide synthase (GCS).
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Paragraph 000404
(2015/04/15)
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- Enantioselective copper(I/II)-catalyzed conjugate addition of nitro esters to β,γ-unsaturated α-ketoesters
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A highly enantioselective Michael addition of nitroacetates to β,γ-unsaturated α-ketoesters was developed by using chiral copper catalysts. The Michael addition products can be obtained in high yields with up to 99 % ee. With these densely functionalized products, the chiral cyclic nitrones, which are important synthetic intermediates, can be obtained in one step. Copyright
- Zhang, Sheng,Xu, Kun,Guo, Fengfeng,Hu, Yanbin,Zha, Zhenggen,Wang, Zhiyong
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supporting information
p. 979 - 982
(2014/02/14)
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- Enantioselective copper-catalyzed conjugate addition of trimethylaluminium to β,γ-unsaturated α-ketoesters
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Not a cop out: The copper-catalyzed asymmetric conjugate addition of organometallic reagents to Michael acceptors is an important methodology for forming a C-C bond in an enantioselective manner. Such an addition of Me 3Al to β,γ-unsaturated α-
- Gremaud, Ludovic,Alexakis, Alexandre
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supporting information; experimental part
p. 794 - 797
(2012/03/09)
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