Organocatalytic Michael–Alkylation Cascade: The Enantioselective Nitrocyclopropanation of Oxindoles

Pesciaioli, Fabio; Righi, Paolo; Mazzanti, Andrea; Bartoli, Giuseppe; Bencivenni, Giorgio

doi:10.1002/chem.201003423

Cited by 149 publications

(54 citation statements)

References 81 publications

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“…More recently, Bartoli et al have reported the enantioselective nitrocyclopropanation of oxindoles 168a-d with bromonitromethane which was induced through hydrogen-bonding activation mode by 9-epi-9-thiourea-9-deoxydihydroquinidine 169 in the presence of NaHCO 3 . [86] As shown in Scheme 46, the corresponding spiro nitrocyclopropyl oxindoles 170a-d were achieved in good to high yields, moderate to high diastereoselectivities, and excellent enantioselectivities of up to 98% ee.…”

Section: Domino Michael-intramolecular Alkylation Reactionsmentioning

confidence: 97%

Recent Developments in Asymmetric Organocatalytic Domino Reactions

2012

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Since about the year 2000, the research area of asymmetric organocatalysis has grown rapidly to become one of the most fascinating and current fields in organic chemistry. In the last years, asymmetric domino reactions have widely benefited from this fast-growing field, as exemplified by the development of an explosive number of novel and powerful asymmetric organocatalytic domino processes, which allowed the easy construction of complex chiral molecular architectures from simple materials with high yields and very often remarkable enantioselectivities in a metal-free environment. Indeed, the possibility to join two or more organocatalytic reactions in one asymmetric domino process has become a challenging goal for chemists, due to several advantages from economical and environmental points of view, avoiding costly protecting groups and time-consuming purification procedures after each step, for example. This review aims to update the latest developments of this hot and fascinating field, covering the literature since the beginning of 2009.

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Section: Domino Michael-intramolecular Alkylation Reactionsmentioning

confidence: 97%

Recent Developments in Asymmetric Organocatalytic Domino Reactions

2012

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“…In 2011, Bartoli and Bencivenni developed a highly efficient asymmetric approach to spiro cyclopropyl oxindoles 7 with three adjacent stereogenic centers based on an organocatalytic Michael–alkylation cascade sequence of methyleneindolinones and halonitroalkanes 5 (Scheme ) 37. The reaction was efficiently catalyzed by the bifunctional catalyst 6 , rendering the final spiro cyclopropyl oxindoles 7 in good yields, diastereoselectivities and enantioselectivities.…”

Section: Three‐membered Fused Ringsmentioning

confidence: 99%

Recent Advances in Asymmetric Organocatalytic Construction of 3,3′‐Spirocyclic Oxindoles

2013

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The asymmetric organocatalysis is definitely one of the most powerful and versatile tools for the rapid construction of various spirocyclic oxindoles. In the past few years, a number of successful strategies based on organocatalysis have been developed for the construction of 3,3′‐spirocyclic oxindoles in high yields and excellent enantioselectivities under mild conditions. In this review, recent advances in this area are summarized and classified according to the spiro ring fused at the 3‐position of the oxindole core.

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“…70 The efficiency of the reaction proved to be highly solvent dependent with the optimum reaction conditions found with methyl t-butyl ether (MTBE) and one equivalent of Na 2 CO 3 . In 2011, Bencivenni and co-workers disclosed the first enantioselective nitrocyclopropanation of 3-alkylidene oxindoles and bromonitroalkyl derivatives with thiourea catalyst 15 (Scheme 23).…”

Section: Scheme 14mentioning

confidence: 99%

Cyclopropanation Reactions☆

Arvidsson¹,

Bose²,

Naicker³

2015

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

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All other uses, reproduction and distribution, including without limitation commercial reprints, selling or licensing copies or access, or posting on open internet sites, your personal or institution's website or repository, are prohibited. For exceptions, permission may be sought for such use through Elsevier's permissions site at: http://www.elsevier.com/locate/permissionusematerial Arvidsson P.I., Bose P.P. and Naicker T. (2014) Cyclopropanation Reactions. In: Reedijk, J. (Ed.) Elsevier Reference Module in Chemistry, Molecular Sciences and Chemical Engineering. Waltham, MA: Elsevier. 23-Jan-15

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Organocatalytic Michael–Alkylation Cascade: The Enantioselective Nitrocyclopropanation of Oxindoles

Abstract: The spiro saga goes on! The title reaction sequence provides the first enantioselective synthesis of spiro nitrocyclopropyl oxindoles. The method provides easy access to these new, biologically inspired compounds from readily available starting materials (see scheme).

Cited by 149 publications

References 81 publications

Recent Developments in Asymmetric Organocatalytic Domino Reactions

Recent Developments in Asymmetric Organocatalytic Domino Reactions

Recent Advances in Asymmetric Organocatalytic Construction of 3,3′‐Spirocyclic Oxindoles

Cyclopropanation Reactions☆

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