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Enantioselective Construction of Spirooxindole-Fused Cyclopentanes
The Journal of Organic Chemistry, 2021The present study reports an asymmetric organocatalytic cascade reaction of oxindole derivates with α,β-unsaturated aldehydes efficiently catalyzed by simple chiral secondary amine. Spirooxindole-fused cyclopentanes were produced in excellent isolated yields (up to 98%) with excellent enantiopurities (up to 99% ee) and moderate to high ...
Vojtěch Dočekal +7 more
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Organic Letters, 2000
[reaction: see text]Reaction of indole amides 5 with tributylstannane gave spiroindolenines 9 which are readily converted into spiropyrrolidinyloxindoles. This tricyclic system is found in a number of interesting natural products.
S T, Hilton +3 more
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[reaction: see text]Reaction of indole amides 5 with tributylstannane gave spiroindolenines 9 which are readily converted into spiropyrrolidinyloxindoles. This tricyclic system is found in a number of interesting natural products.
S T, Hilton +3 more
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Spirooxindoles as Potential Pharmacophores
Mini-Reviews in Medicinal Chemistry, 2017The spiroindole heterocyclic scaffold is found in many natural products and has been identified as an important bioactive agent. Over the past few decades, various spiroindole-containing compounds have been reported to possess biological properties and hence found in the structure of many synthetic pharmaceuticals.
Siva S, Panda +3 more
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Expeditious entry into carbocyclic and heterocyclic spirooxindoles
Organic & Biomolecular Chemistry, 2022Recent advances in the chemistry of base-, metal-, nano-metal and organo-catalyst mediated achiral and chiral versions of the structurally diverse and pharmaceutically relevant spirooxindoles are gently reviewed.
Madhu Ganesh, Shammy Suraj
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Organocatalytic Asymmetric Synthesis of Spirooxindole Embedded Oxazolidines
The Journal of Organic Chemistry, 2021The first organocatalytic asymmetric synthesis of spirooxindole embedded oxazolidines has been developed via a domino reaction involving hemiaminal formation, followed by an unprecedented aza-Michael reaction between isatin derived N-Boc ketimines and γ-hydroxy enones.
Chandrakanta Parida +3 more
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Catalytic asymmetric synthesis of spirooxindoles: recent developments
Chemical Communications, 2018The past four years have witnessed significant developments in the field of the catalytic asymmetric synthesis of spirooxindoles, and this feature article outlines the recent progress in this area, including the contributions of our group. This article is divided into sections according to the size and type of the generated spiro-ring fused at the C3 ...
Guang-Jian Mei, Feng Shi
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Diastereoselective Synthesis and Structure of Spirooxindole Derivatives
HETEROCYCLES, 2003Spiroindolinonisoxazolines (4 and 5h) are prepared from (E)- 1 or (Z)-3-arylidene-2-oxindoles (2) by nitrile oxide cycloaddition reactions. Only one regioisomer is detected in all cases, and the observed complete diastereoselection is established by unambigous structural assignments.
RISITANO, Francesco +4 more
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Strategies for the enantioselective synthesis of spirooxindoles
Organic & Biomolecular Chemistry, 2012Oxindoles and spirooxindoles are important synthetic targets that are often considered to be prevalidated with respect to their biological activity and applications for pharmaceutical lead discovery. This review features efficient strategies for the enantioselective synthesis of spirocyclic oxindoles, focusing on reports in 2010 and 2011.
Nicolas R, Ball-Jones +2 more
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Titanium-Catalyzed Stereoselective Synthesis of Spirooxindole Oxazolines
Organic Letters, 2010A regio- and stereoselective cyclization between isatins and 5-methoxyoxazoles has been developed using catalytic titanium(IV) chloride (10 or 20 mol %) to afford spiro[3,3'-oxindoleoxazolines] in excellent yield (up to 99%) and diastereoselectivity (dr >99:1). Substitution at the 4-position of the oxazole controls nucleophilic attack to provide either
Joseph J, Badillo +3 more
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Superacid-Promoted synthesis of spirooxindoles
Tetrahedron Letters, 2023Jacob C. Hood +2 more
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