- Phosphine-Catalyzed [3 + 2] Annulation of Morita-Baylis-Hillman Carbonates with Isoxazole-Based Alkenes
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A phosphine-catalyzed [3 + 2] annulation of Morita-Baylis-Hillman (MBH) carbonates with 3-methyl-4-nitro-5-styrylisoxazoles has been developed to afford various multifunctional isoxazoles in moderate to good yields with moderate to excellent diastereoselectivities. With a spirocyclic chiral phosphine as the catalyst, up to 89% ee was obtained.
- Liao, Jianning,Dong, Jipan,Xu, Jiaqing,Wang, Wei,Wu, Yongjun,Hou, Yuxia,Guo, Hongchao
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supporting information
p. 2090 - 2099
(2021/02/05)
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- Ligand-Dependent Regiodivergent Enantioselective Allylic Alkylations of α-Trifluoromethylated Ketones
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The asymmetric introduction of the CF3 unit is a powerful tool for modifying pharmacokinetic properties and slowing metabolic degradation in medicinal chemistry. A catalytic and enantioselective addition of α-CF3 enolates allows for expeditious access to
- Zhu, Yi,Ni, Yifan,Lu, Chenxi,Wang, Xiaochen,Wang, Yi,Xue, Xiao-Song,Pan, Yi
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supporting information
p. 2443 - 2448
(2021/04/05)
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- Phosphine-catalyzed [3+2] cycloaddition of Morita—Baylis—Hillman carbonates to isothiocyanates in the synthesis of adamantane-containing trisubstituted aminothiophenes
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An addition of the Morita—Baylis—Hillman (MBH) carbonates to adamantane-containing isothiocyanates was studied. The MBH carbonates react with 1-(4-isothiocyanatophenyl)-adamantane in the presence of triphenylphosphine to give 5-aryl-substituted adamantane
- Abel, A. S.,Averin, A. D.,Beletskaya, I. P.,Butov, G. M.,Zenkov, I. S.
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p. 880 - 884
(2021/06/07)
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- Synthesis of β-Lactams via Enantioselective Allylation of Anilines with Morita-Baylis-Hillman Carbonates
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Enantioenriched β-lactams are accessed via enantioselective allylation of anilines with Morita-Baylis-Hillman carbonates followed by a base-promoted cyclization. The resulting 3-methyleneazetidin-2-ones are amenable to diastereoselective functionalization
- Krieck, Sven,Lange, Markus,Schüler, Philipp,Vilotijevic, Ivan,Westerhausen, Matthias,Zi, You
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supporting information
p. 575 - 580
(2020/03/27)
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- Organocatalytic Allylic Amination of Morita-Baylis-Hillman Carbonates
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An organocatalytic asymmetric allylic amination of Morita-Baylis-Hillman carbonates with aromatic amines in the presence of β-isocupreidine is described. Chiral allylic amines were obtained in almost quantitative yields (90-96%) with moderate enantioselectivity. Recrystallization afforded products in good yields (45-73%) and high optical purity (82-99% ee). This method provides a facile and efficient route to obtain optically active β-lactams, including the building block of the cholesterol-lowering drug Ezetimibe.
- Formánek, Bed?ich,?imek, Michal,Kamlar, Martin,Císa?ová, Ivana,Vesely, Jan
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p. 907 - 920
(2019/02/10)
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- Enantioselective dearomative [3+2] cycloaddition of 2-nitrobenzofurans with aldehyde-derived Morita-Baylis-Hillman carbonates
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The phosphine-catalyzed asymmetric dearomative [3+2] cycloaddition of 2-nitrobenzofurans with aldehyde-derived Morita-Baylis-Hillman (MBH) carbonates or allenoate was developed. The reaction with MBH carbonates resulted in a series of cyclopentabenzofurans containing three contiguous stereocenters with good to high yields, diastereoselectivities and enantioselectivities. The use of allenoate also gave the target product with moderate enantioselectivity.
- Yang, Xin-He,Li, Jian-Ping,Wang, Dong-Chao,Xie, Ming-Sheng,Qu, Gui-Rong,Guo, Hai-Ming
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supporting information
p. 9144 - 9147
(2019/08/07)
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- Direct Synthesis of Dihydropyrrolo[2,1-a]Isoquinolines through FeCl3 Promoted Oxidative Aromatization
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We have developed a straightforward FeCl3 promoted synthesis of dihydropyrrolo[2,1-a]isoquinolines through formal (3+2) cycloaddition/oxidative aromatization cascade of dihydroisoquinoline with Morita-Baylis-Hillman carbonates (up to 96% yield)
- Cui, Hai-Lei,Jiang, Lu,Tan, Hao,Liu, Si
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supporting information
p. 4772 - 4780
(2019/10/28)
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- Effective and diastereoselective preparation of dispiro[cyclopent-3′-ene]bisoxindoles: Via novel [3 + 2] annulation of isoindigos and MBH carbonates
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A novel and diastereoselective [3 + 2] annulation of isoindigos and Morita-Baylis-Hillman carbonates has been developed for the highly efficient and one-step preparation of highly steric dispiro[cyclopent-3′-ene]bisoxindoles with two all-carbon quaternary
- Ren, Hong-Xia,Peng, Lin,Song, Xiang-Jia,Liao, Li-Guo,Zou, Ying,Tian, Fang,Wang, Li-Xin
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supporting information
p. 1297 - 1304
(2018/03/06)
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- Umpolung of o-Hydroxyaryl Azomethine Ylides: Entry to Functionalized ?-Aminobutyric Acid under Phosphine Catalysis
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A phosphine-catalyzed reaction between o-hydroxyaryl azomethine ylides and MBH carbonates provides access to highly functionalized ?-aminobutyric acid derivatives in moderate to good yields. Mechanistically, the reaction involves a phosphine-catalyzed tandem SN2′/2-aza-Cope rearrangement/intramolecular addition process.
- Chen, Qingqing,Bao, Yishu,Yang, Xiuqin,Dai, Zonghao,Yang, Fulai,Zhou, Qingfa
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p. 5380 - 5383
(2018/09/13)
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- A cascade synthesis of: S -allyl benzoylcarbamothioates via Mumm-type rearrangement
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A catalyst and solvent free synthesis of S-allyl benzoylcarbamothioates has been achieved from the in situ generated benzoylcarbonimidothioates obtained by reacting MBH alcohols with aroyl isothiocyanates. An intramolecular thia-Michael addition of the in
- Dahiya, Anjali,Ali, Wajid,Alam, Tipu,Patel, Bhisma K.
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supporting information
p. 7787 - 7791
(2018/11/21)
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- Studies on Pumiliotoxin A Alkaloids: An Approach to Preparing the Indolizidinic Core by Intramolecular Diastereoselective N-Heterocyclic Carbene Catalyzed Benzoin Reaction
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In this article, we describe the development of a convergent organocatalytic strategy to prepare the indolizidinic core of the pumiliotoxin A alkaloid family. The key step of the proposed strategy is based on a diastereoselective N-heterocyclic carbene ca
- Correia, José Tiago M.,Acconcia, Laís V.,Coelho, Fernando
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supporting information
p. 1972 - 1976
(2016/04/26)
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- Synthesis of Chiral α-Trifluoromethylamines with 2,2,2-Trifluoroethylamine as a "building Block"
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The β-isocupreidine, a cinchonine derived alkaloid, catalyzed asymmetric SN2′-SN2′ reaction between N-2,2,2-trifluoroethylisatin ketimines and MBH type carbonates was realized in a simple and efficient way. A series of chiral α-trifl
- Li, Xiaoyuan,Su, Jinhuan,Liu, Zhourujun,Zhu, Yuanyuan,Dong, Zhenghao,Qiu, Shuai,Wang, Jiayi,Lin, Li,Shen, Zhiqiang,Yan, Wenjin,Wang, Kairong,Wang, Rui
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supporting information
p. 956 - 959
(2016/03/15)
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- Catalytic asymmetric one-pot synthesis of α-methylene-γ-lactams
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An organocatalytic enantioselective synthesis of α-methylene-γ- lactams has been developed. The reaction between protected 2-aminomalonates and Morita-Baylis-Hillman carbonates is catalyzed by chiral Lewis bases to afford the corresponding lactams in exce
- Companyó, Xavier,Geant, Pierre-Yves,Mazzanti, Andrea,Moyano, Albert,Rios, Ramon
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- Catalyst-free synthesis of skipped dienes from phosphorus ylides, allylic carbonates, and aldehydes via a one-pot SN2′ allylation-wittig strategy
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A catalyst-free allylic alkylation of stabilized phosphorus ylides with allylic carbonates via a regioselective SN2′ process is presented. Subsequent one-pot Wittig reaction with both aliphatic and aromatic aldehydes as well as ketenes provides structurally diverse skipped dienes (1,4-dienes) in generally high yields and moderate to excellent stereoselectivity with flexible substituent patterns. This one-pot S N2′ allylation-Wittig strategy constitutes a convenient and efficient synthetic method for highly functionalized skipped dienes from readily available starting materials.
- Xu, Silong,Zhu, Shaoying,Shang, Jian,Zhang, Junjie,Tang, Yuhai,Dou, Jianwei
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p. 3696 - 3703
(2014/05/06)
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- A facile, versatile, and mild morita-baylis-hillman-type reaction for the modular one-pot synthesis of highly functionalized MBH adducts
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Morita-Baylis-Hillman derivatives have been extensively investigated as intermediates in the preparation of important classes of compounds. However, there are intrinsic limitations regarding the structure of the Michael electrophile acceptors, the aldehydes, and the catalysts. Therefore, this transformation has several drawbacks, including, for example, its long reaction times. Herein we present a simple, general, fast, and high-yielding protocol for the one-pot synthesis of Morita-Baylis-Hillman derivatives. Our approach is driven by a lithium selenolate Michael/aldol operation with concomitant O-functionalization/selenoxide elimination cascade sequences. Here we describe a one-pot, fast, and high-yielding methodology for the synthesis of different Morita-Baylis-Hillman derivatives by a four-component cascade reaction. The cascade is based on a Michael/aldol/O-functionalization/selenoxide elimination sequence. This protocol completely avoids the manipulation of selenium species with an unpleasant odor.
- Sousa, Bruno A.,Dos Santos, Alcindo A.
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scheme or table
p. 3431 - 3436
(2012/07/31)
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- Construction of adjacent quaternary and tertiary stereocenters via an organocatalytic allylic alkylation of Morita-Baylis-Hillman carbonates
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Racemic Baylis-Hillman carbonates can be converted in densely functionalized products by reaction with cyano esters in the presence of a catalytic amount of a modified Cinchona alkaloid in high enantioselectivities and fair diastereoselectivities. A ratio
- Van Steenis, Dirk Jan V. C.,Marcelli, Tommaso,Lutz, Martin,Spek, Anthony L.,Van Maarseveen, Jan H.,Hiemstra, Henk
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p. 281 - 286
(2008/02/05)
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