Chemists Clean Up Synthesis With One-Pot Reactions

Hall, Nina

doi:10.1126/science.266.5182.32

Cited by 213 publications

(83 citation statements)

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“…In light of this report, we focused our attention on the [3,3] sigmatropic rearrangement. Emmanuelle, who joined the group very shortly after Tania defended her Ph.…”

Section: Scheme 32mentioning

confidence: 99%

Our Recent Contribution to the Field of Anionic Domino Transformations

Rodríguez

1999

Synlett

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This personal account presents our recent contributions to the field of anionic domino transformations involving combinations of nonidentical reactions. Our choice was to study the feasibility of processes initiated in the presence of very simple and user friendly bases such as potassium carbonate (K 2 CO 3 ) or 1, 8-diazabicyclo[5.4.0]undec-7-ene (DBU), involved in simple and wellknown transformations such as dehydrohalogenation, isomerization, Michael addition, aldolization, nucleophilic substitution, and retro-Dieckmann reaction. Sequential combinations of these different reactions have led to the proposal of new stereoselective one-pot methodologies, including up to five different steps, allowing the facile and efficient preparation of a variety of powerful synthetic intermediates such as epoxides, cis-1,2-diols, acylfurans, bridged bicyclic compounds, functionalized seven-and eight-membered rings, arylidenecycloalkanones, and substituted vinyl-, allenyl-or methylenetetrahydrofurans and pyrrolidines.Among the growing number of useful sequential transformations used in organic chemistry, domino reactions, 1 which are also widely involved in nature, emerge as powerful synthetic tools. This well known concept 2 is of considerable current interest in modern organic synthesis since it enables the rapid assembly of products by combining several different reactions in a one-pot process under the same experimental conditions and without isolating the intermediates. This allows both an economical and ecological access to complex molecules. 3 Moreover, the synthetic value of such cascade sequences is even amplified if they also create multiple stereogenic centers with total stereocontrol. While today metal-catalyzed sequences seem to lead the way, 4 the aim of this personal account is to stress the fact that there is still room for new ionic processes which yet constitute the largest family of domino reactions. In this context, our contribution started a few years ago when we decided to look for new transformations useful for the synthesis of bioactive targets. In order to optimize efficiency we evaluated three important criteria: selectivity, accessibility of the substrates and the reagents, and cleanness in order to minimize product purification and waste production.Our choice was to study the feasibility of anionic domino reactions initiated by very simple and user friendly bases involved in simple and well-known transformations such as dehydrohalogenation, isomerization, Michael addition, aldolization, nucleophilic substitution, and retro-Dieckmann reaction.In early 1990, in collaboration with my friend and former mentor Jean-Pierre Dulcère, we initiated a program aimed at the development of the synthetic potential of functionalized haloethers easily obtained by cohalogenation of olefins in THF. 5 Our first thought was to use trans-b,d-dihalogenated ethers as direct precursors of allyl vinyl ethers through a sequence involving a double dehydrohalogenation followed by selective isomerization of the resulting double ...

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“…In light of this report, we focused our attention on the [3,3] sigmatropic rearrangement. Emmanuelle, who joined the group very shortly after Tania defended her Ph.…”

Section: Scheme 32mentioning

confidence: 99%

Our Recent Contribution to the Field of Anionic Domino Transformations

Rodríguez

1999

Synlett

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“…Under these considerations, one-pot sequential [64,65] and multicomponent [66] reactions have emerged as an important means of achieving these goals. One-pot sequential and multicomponent reactions circumvent the need to isolate and purify synthetic intermediates, achieving the economic and environmental goals of saving bulk materials, development time, and labor.…”

Section: One-pot Sequential Aldol Reactionsmentioning

confidence: 99%

Supersilyl Protective Groups in Aldol Reactions

Brady

Yamamoto

2013

Modern Methods in Stereoselective Aldol Reactions

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“…However, it would be much more efficient if one could form several bonds in one sequence without isolating the intermediates, changing the reaction conditions, or adding reagents (Tietze and Beifuss, 1993;Waldmann, 1995;Hall, 1994). Thus, multicomponent condensation was an active field in the research of organic reactions because it can readily construct complicated heterocyclic scaffolds (Yu et al, 2011;Dondoni and Massi, 2006).…”

Section: Introductionmentioning

confidence: 98%

Development of one-pot three component reaction for the synthesis of N′-aryl-N-cyanoformamidines, essential precursors of formamidine pesticides family

Nino

Maiuolo

Nardi

et al. 2016

Arabian Journal of Chemistry

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Efficient one-pot three component reaction of aniline derivatives with cyanoamide and triethyl orthoformate at reflux in toluene affords N 0 -aryl-N-cyanoformamidines in high yields just by the distillation of the azeotrope toluene/ethyl alcohol. Labelled d 9 -Amitraz is prepared by the application of this procedure in the synthesis of formamidine pesticides family. ª 2015 The Authors. Production and hosting by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

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Chemists Clean Up Synthesis With One-Pot Reactions

Cited by 213 publications

References 0 publications

Our Recent Contribution to the Field of Anionic Domino Transformations

Our Recent Contribution to the Field of Anionic Domino Transformations

Supersilyl Protective Groups in Aldol Reactions

Development of one-pot three component reaction for the synthesis of N′-aryl-N-cyanoformamidines, essential precursors of formamidine pesticides family

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