Organocatalyzed Cascade Aza‐Michael/Michael Addition for the Asymmetric Construction of Highly Functionalized Spiropyrazolone Tetrahydroquinolines

Li, Junhua; Du, Da‐Ming

doi:10.1002/asia.201402706

Cited by 68 publications

(20 citation statements)

References 66 publications

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“…Du and co‐workers reported the domino aza‐Michael/Michael reaction between 499 and 628 , using the cyclohexanediamine‐derived squaramide 702 as the catalyst, and obtained the spiro‐pyrrolidine‐pyrazolone derivatives 701 in good to high stereoselectivities . These authors also realized a similar domino aza‐Michael/Michael reaction between 499 and 64 for the highly stereoselective synthesis of spiro‐tetrahydroquinoline derivatives 703 , using a quinidine‐derived squaramide 634 as the catalyst …”

Section: Multifunctional Catalystsmentioning

confidence: 90%

Recent Progress in Organocatalytic Asymmetric Domino Transformations

2017

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Sustainability in chemical synthesis is a major aspect of the current synthetic endeavors and, therefore,m imicking the biological process in the laboratory nowadays has the highest priority.T owards achieving this goal, designingorganic reactions in domino mode rathert han the multistep synthetic pathways andu sing organocatalysisi nstead of metal catalysis have received al ot of attention due to the inherenta dvantageso ft hese processes in terms of synthetic efficiencya nd sustainability.A saresult, the field of asymmetric organocatalytic domino reactions has witnessed tremendous progress in recent years.T his review attempts to summarize the latest developments in asymmetric organocatalyzed domino reactions since 2012, with the emphasis on the catalysts andr eactionm odes.D iscussions on the reactionm echanismsa nd the applications of the developed domino reactionm ethodsi nt he synthesis of biologically active molecules and natural products are also includedwhen appropriate.

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Section: Multifunctional Catalystsmentioning

confidence: 90%

Recent Progress in Organocatalytic Asymmetric Domino Transformations

2017

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“…A diastereo‐ and enantioselective cascade aza‐Michael/Michael addition of 2‐tosylaminoenones 111 to unsaturated pyrazolones 78 catalyzed by a squaramide X was developed to afford novel chiral spiropyrazolone tetrahydroquinolines 117 containing three contiguous stereocenters, including one quaternary center (Scheme ) . This cascade reaction proceeded well with only 2 mol% chiral bifunctional squaramide catalyst to give the desired products in excellent yields (43‐99 % yield) with excellent diastereoselectivity (9:1‐>25:1 dr ) and high enantioselectivity (60‐91 % ee ).…”

Section: Squaramide‐catalyzed Asymmetric Cascade Reactionsmentioning

confidence: 99%

Squaramide‐Catalyzed Asymmetric Reactions

Zhao

2017

The Chemical Record

104

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Bifunctional squaramides have emerged as powerful hydrogen-bonding catalysts for promoting a wide array of useful asymmetric reactions, which provides convenient methods for the construction of complex molecular structures and chiral biologically active compounds. This review highlights the recent advances of our research group in the chiral squaramide-catalyzed asymmetric reactions, including Michael addition, Mannich reaction, aza-Henry reaction, Strecker reaction as well as cascade or sequential reactions.

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“…In 2014, the Du group studied an organocatalyzed aza‐Michael/Michael addition between unsaturated pyrazolones 1 and substituted 2‐tosylaminochalcones 76 to firstly realize the asymmetric synthesis of spiropyrazolone tetrahydroquinolines 77 with three contiguous stereocenters (Scheme ) . In the screening of the reaction conditions, bifunctional organocatalysts, catalyst loading, reaction medium, temperature and the amount of solvent were investigated.…”

Section: Organocatalytic Asymmetric Synthesis Of Spiropyrazolones Fusmentioning

confidence: 99%

Catalytic Asymmetric Synthesis of Spiropyrazolones and their Application in Medicinal Chemistry

Xie

Peng

et al. 2019

The Chemical Record

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Chiral spiropyrazolones are unique frameworks widely found in a large family of medicinally relevant compounds with various biological activities. Substantial research efforts have been invested toward stereoselectively by constructing spiro‐cyclic structures. Over the past years, remarkable progress has been made in the organo‐ and metal‐catalyzed asymmetric synthesis of spiropyrazolones through the utilization of accessible simple pyrazolone derivatives as raw materials. This review is organized according to the size of the spiro‐ring fused at the 4‐position of the pyrazolone framework. In the last part, the bio‐evaluations of chiral spiropyrazolones for drug discovery are summarized.

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Organocatalyzed Cascade Aza‐Michael/Michael Addition for the Asymmetric Construction of Highly Functionalized Spiropyrazolone Tetrahydroquinolines

Cited by 68 publications

References 66 publications

Recent Progress in Organocatalytic Asymmetric Domino Transformations

Recent Progress in Organocatalytic Asymmetric Domino Transformations

Squaramide‐Catalyzed Asymmetric Reactions

Catalytic Asymmetric Synthesis of Spiropyrazolones and their Application in Medicinal Chemistry

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