Asymmetric One‐Pot Four‐Component Coupling Reaction: Synthesis of Substituted Tetrahydropyrans Catalyzed by Diphenylprolinol Silyl Ether

Ishikawa, Hayato; Sawano, Satoshi; Yasui, Yusuke; Shibata, Yusuke; Hayashi, Yujiro

doi:10.1002/anie.201005386

Cited by 71 publications

(19 citation statements)

References 62 publications

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“…In 2011, Hayashi synthesized fully substituted ( anti , syn , syn )‐tetrahydropyrans 20 in excellent stereoselectivity through a cascade reaction. Chiral secondary amine 18 ‐catalyzed enantioselective Michael reaction of aldehydes with nitroalkenes, and then the following Henry reaction of the resulting intermediate with α‐carbonyl aldehydes and acetalization reaction happened promoted by tertiary amine Et 3 N …”

Section: Diastereodivergency By Two Chiral Catalystsmentioning

confidence: 99%

Catalytic Strategies for Diastereodivergent Synthesis

Lin

Feng

2017

Chemistry A European J

228

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Chiral molecules with multiple stereocenters are widely distributed in nature and drugs. Asymmeric catalysis has allowed the formation of a chiral molecule's enantiomers with equal ease by applying the enantiomeric pair of a chiral catalyst. However, the diastereodivergent synthesis is a great challenge because the formation of one of the diastereomers is inherently preferred in most reactions. Under the efforts of chemists, elegant strategies have been developed to full control of absolute and relative stereochemical configurations. In this Minireview, we highlight the significant advances achieved in this field, and present the diastereo-control mechanism in the appropriate place on the expectation that new diastereodivergent strategies can be inspired and more types of enantioselective diastereodivergent reactions can be realized.

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Section: Diastereodivergency By Two Chiral Catalystsmentioning

confidence: 99%

Catalytic Strategies for Diastereodivergent Synthesis

Lin

Feng

2017

Chemistry A European J

228

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“…4.1 手性氢化吡喃衍生物的不对称合成手性四氢吡喃骨架广泛存在于具有生物活性的天然产物和药物分子中, 开发构建手性四氢吡喃骨架的新方法是有机及药物化学领域的重要课题 [46] . 2011 年, Ishikawa 等 [47] 报道了硝基烯参与的四组分"一锅法"不对称 Michael/Henry/缩醛/异构化串联反应, 合成了两类硝基手性构型相反的四氢吡喃衍生物 66, 67 (Scheme 12). 该反应利用二苯基脯氨醇甲基硅醚(1b)为手性催化剂, 发生脂肪醛(4)和硝基烯(5)的不对称 Michael 加成, 得到的 Michael 加成中间体 I 与醛(68a 或 4d)发生缩醛反应.…”

Section: 其它类型化合物不对称合成unclassified

Advances in Multicomponent Asymmetric Cascade Synthesis Involving Nitroolefin Catalyzed by Diarylprolinol Derivatives

Liang¹,

Han²,

Wang³

et al. 2020

Chin. J. Org. Chem.

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Nitroolefin is an important class of organic synthons. The synthetic method of multicomponent asymmetric cascade reactions involving nitroolefin catalyzed by diarlyprolinol derivatives is quite important for the construction of complex chiral compounds. It is widely used in organic synthesis and new drugs development. In this paper, the multicomponent asymmetric cascade synthesis involving nitroalkenes catalyzed by diarlyprolinol derivatives is comprehensively summarized based on the type of target compounds. In detail, the catalyst systems, reaction mechanisms, experimental results, reaction advantages, existing problems and limitations for this synthetic method are introduced respectively. The future development for this synthetic period is further evaluated as well.

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“…[19][20][21][22][23][24][25] In particular, an efficient method is neededf or asymmetrics ynthesis of heterocyclic structures with more than one nitrogen atom containing four contiguous stereogenic centers. [26] As parto fo ur ongoing efforts to transform readily available substrates stereoselectively into synthetically important chiral heterocycles, [27][28][29][30][31][32][33] we envisaged accessing the chiral hexahydropyridazine scaffold from aldehydes,n itroolefins, and azodicarboxylates by performing ac ascade reactiont hat consisted of an initial secondary amine-catalyzed Michael reaction [34][35][36][37][38][39] followed by intermolecular a-amination and intramolecular hemiaminalization (Scheme 1). [40] It is worth noting that asymmetric organocatalytic cascade reactions can build complex chiral skeletons often with excellent stereoselectivity under environmentally friendly conditions, and such cascade reactions have become increasingly important for total synthesis [41][42][43][44][45] and the construction of chiral molecular libraries.…”

Section: Introductionmentioning

confidence: 99%

Core‐Scaffold‐Inspired Asymmetric Synthesis of Polysubstituted Chiral Hexahydropyridazines that Potently Inhibit Breast Cancer Cell Proliferation by Inducing Apoptosis

Leng

Zingales

et al. 2015

Chemistry A European J

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The highly enantioselective preparation of pharmacologically interesting hexahydropyridazine derivatives based on a multicomponent cascade reaction is described. This one-pot approach utilizes an organocatalytic Michael reaction followed by intermolecular α-amination and intramolecular hemiaminalization to yield a chiral pyridazine backbone with contiguous stereogenic centers and multiple functional groups in good yield and with high stereoselectivity. Compounds synthesized by this method potently inhibited proliferation of MCF-7 breast cancer cells. Mechanistic studies suggest that compound 5 c exerts these anticancer effects by inducing apoptosis through extracellular signal related kinase (ERK)- and poly(adenosine diphosphate ribose) polymerase (PARP)-regulated pathways, as well as mitochondrial pathways.

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Asymmetric One‐Pot Four‐Component Coupling Reaction: Synthesis of Substituted Tetrahydropyrans Catalyzed by Diphenylprolinol Silyl Ether

Cited by 71 publications

References 62 publications

Catalytic Strategies for Diastereodivergent Synthesis

Catalytic Strategies for Diastereodivergent Synthesis

Advances in Multicomponent Asymmetric Cascade Synthesis Involving Nitroolefin Catalyzed by Diarylprolinol Derivatives

Core‐Scaffold‐Inspired Asymmetric Synthesis of Polysubstituted Chiral Hexahydropyridazines that Potently Inhibit Breast Cancer Cell Proliferation by Inducing Apoptosis

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