Brønsted Acid Catalyzed Asymmetric Diels–Alder Reactions: Stereoselective Construction of Spiro[tetrahydrocarbazole-3,3′-oxindole] Framework

Wang, Yang; Tu, Man‐Su; Yin, Lei; Sun, Meng; Shi, Feng

doi:10.1021/acs.joc.5b00198

Cited by 102 publications

(22 citation statements)

References 60 publications

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“…However, the N ‐unprotected 2‐vinylindole 73 favored the feasibility of the reaction. The chiral catalyst 74 acted as a Brønsted acid/Lewis base, being a bifunctional catalyst to active simultaneously both an amide group of 72 and an amine group of 73 via hydrogen‐bonding interaction to provide the spiro[tetrahydrocarbazole‐3,3'‐oxindole] 75 , as depicted in Scheme …”

Section: Asymmetric Synthesis Of Spirooxindoles In One Stepmentioning

confidence: 99%

Organocatalytic Synthesis of Chiral Spirooxindoles with Quaternary Stereogenic Centers

Sansinenea

Martínez

2020

Eur J Org Chem

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The structure of spirooxindoles is present in a large number of natural compounds, with relevant and different biological activities. The organic synthesis of these compounds has been a synthetic challenge due to the fusion of two or more cycles with one or more contiguous stereogenic centers. In this review, it has been described, the feasibility of organocatalytic asymmetric synthesis for the achievement of chiral spirooxindoles through two‐ or three‐component reaction in the presence of a chiral organocatalyst producing the compounds with high yield, high diastereoselectivity and with high enantiomeric purity. This review covers literature from 2010 to 2019. The most explored reactions for this purpose have been 1,3‐dipolar cycloaddition, Diels‐Alder and nucleophilic heterocyclic carbenes reactions, where their reaction mechanisms showed in this review are an approach of a possible mechanism.

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Section: Asymmetric Synthesis Of Spirooxindoles In One Stepmentioning

confidence: 99%

Organocatalytic Synthesis of Chiral Spirooxindoles with Quaternary Stereogenic Centers

Sansinenea

Martínez

2020

Eur J Org Chem

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“…Followed by this discovery, in 2015, Shi and co‐workers revealed the synthesis of spiro[tetrahydrocarbazole‐3,3′‐oxindole] 24 architecture. Typically, it involved the asymmetric Diels‐Alder reactions between 2‐vinylindoles 23 and methyleneindolinones 20 catalyzed by chiral phosphoric acid 25 (Scheme ) …”

Section: [4+2]/diels‐alder Reactionmentioning

confidence: 99%

Reliability of Click Chemistry on Drug Discovery: A Personal Account

Shankaraiah

Sakla

Laxmikeshav

et al. 2019

The Chemical Record

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The unprecedented efficiency, reliability and adaptability in drug discovery, with the growing number of applications and impact, have made Click Chemistry fascinating to the scientific community. The specificity, biocompatibility along with other principles of click chemistry offers a reliable platform for the synthesis of drug-like molecules that can expedite the drug discovery process. This account summarizes such successes of versatile click reactions from our research group towards the development of functional molecules.

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“…Similarly, enantioselective cycloadditions between 2‐vinylindoles and methyleneindolinones occur through a hydrogen‐bonding activation mode. In particular, a cinchonidine‐squaramide catalyst and a chiral phosphoric acid were recently employed for the stereoselective construction of a spirotetrahydrocarbazole‐oxindole framework. In the first work, a plethora of hydrogen‐bond‐donor chiral catalysts ranging from cinchonine‐derived thiourea to cinchonidine‐thiourea and cinchonidine‐based squaramides were tested in a model reaction, and the best reaction conditions were applied to the synthesis of a series of functionalized carbazole‐spirooxindoles (Scheme ).…”

Section: [4+2] Cycloaddition Reactions Of 2‐ and 3‐vinylindolesmentioning

confidence: 99%

2‐ and 3‐Vinylindoles as 4π Components in Cycloaddition Reactions

Rossi¹,

Abbiati²,

Pirovano³

2017

Eur J Org Chem

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The review summarizes the most recent achievements in the chemistry of 2‐vinylindoles and 3‐vinylindoles. In particular, we focus on the behavior of these compounds as dienes in cycloaddition reactions. The majority of the literature in this field deals with [4+2] cycloaddition, and only one report of [4+1] cycloaddition has appeared in the literature until now. Thus, the main section reviews [4+2] cycloaddition with activated cyclic and acyclic dienophiles under Lewis‐acid catalysis or organocatalysis conditions. In addition, cycloadditions performed with simple π‐systems as dienophiles, occurring through activation by transition‐metal catalysts, are reviewed. This section mainly involves the use of allenes as dienophiles under gold catalysis conditions. In both cases, the authors report excellent levels of diastereoselectivity and enantioselectivity. Two separate subsections deal with the synthesis of natural compounds and with the use of methyleneindolinones as dienophiles.

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Brønsted Acid Catalyzed Asymmetric Diels–Alder Reactions: Stereoselective Construction of Spiro[tetrahydrocarbazole-3,3′-oxindole] Framework

Cited by 102 publications

References 60 publications

Organocatalytic Synthesis of Chiral Spirooxindoles with Quaternary Stereogenic Centers

Organocatalytic Synthesis of Chiral Spirooxindoles with Quaternary Stereogenic Centers

Reliability of Click Chemistry on Drug Discovery: A Personal Account

2‐ and 3‐Vinylindoles as 4π Components in Cycloaddition Reactions

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