Selectivity Control in Lewis Acid Catalyzed Regiodivergent Tandem Cationic Cyclization/Ring Expansion Terminated by Pinacol Rearrangement

Liu, Lu; Zhang, Junliang

doi:10.1002/anie.200901628

Cited by 77 publications

(23 citation statements)

References 52 publications

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“…They also showed that the same chemistry could be terminated by a pinacol rearrangement by incorporating cyclopropyl group instead of phenyl to synthesize napthalen-2(1H)-ones or differently substituted naphthalenes. [287] Gung et al Au(III)-catalyst (Scheme 71). In this reaction, the regiochemistry of the product is controlled by the position of the acetoxy group in the macrocyclic propargylic acetate 312 along with gold catalyst in different valency state.…”

Section: Miscellaneous Rearrangementsmentioning

confidence: 99%

Regio‐ and Site‐selective Molecular Rearrangements by Homogeneous Gold Catalysis

Praveen

2020

Asian J Org Chem

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Homogeneous gold catalysis for connection and disconnection of carbon-carbon (CÀ C) as well as carbonheteroatom (CÀ X) bond constitutes an important zone in molecular chemistry, since all new or existing organic synthesis relies on the transformation of these chemical bonds. Among the diaspora of molecular transformations, rearrangement and shift reactions occupy a special place in organic chemistry, as they enable the synthesis of molecules of increased complexity from simple precursors. However, the rearrangement in substrates possessing more than one potential reaction site produce more than one isomer and could result in regioselective issues. This challenge of selective synthesis of one regisomer over the other was fairly addressed by gold catalysis on various occasions. To this end, the prowess of homogeneous gold catalysis towards regioselective molecular rearrangement reactions and the contributing parameters are comprehensively reviewed. Also, synthetic applicability of regioselective rearrangements by gold catalysis in total and formal synthesis of several natural products was emphasized.This review also covers the emergence of gold catalyzed migratory/shift selective reactions and could be beneficial for synthetic and medicinal chemists.

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Section: Miscellaneous Rearrangementsmentioning

confidence: 99%

Regio‐ and Site‐selective Molecular Rearrangements by Homogeneous Gold Catalysis

Praveen

2020

Asian J Org Chem

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“…3). 133 In addition, the use of TfOH as catalyst leads to variable mixtures of the corresponding acyl substituted naphthalenes and benzo[a]fluorenols, being the latter the major ones. 131 This alternative pathway is explained by a Friedel-Crafts type cyclization of the intermediate alkenyl cation, generated as proposed above, followed by protodemetalation and double bond isomerization.…”

Section: Scheme 43 Gold-catalyzed Cycloaromatization Of Push-pull 1mentioning

confidence: 99%

“…133 Thus, when employing Moreover, the starting material is recovered when a 2,2'-di(alkynyl)biphenyl having a strong electrondeficient aryl ring in both acetylenes is treated under the optimal reaction conditions, whereas the use of unsymmetrical 2,2'-di(alkynyl)biphenyls leads to complex mixtures.…”

Section: Scheme 45 Cycloaromatization Of O-(alkynyl)styrenes With Camentioning

confidence: 99%

1,3-Dien-5-ynes: Versatile Building Blocks for the Synthesis of Carbo- and Heterocycles

et al. 2016

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ABSTRACT:1,3-Dien-5-ynes have been extensively used as starting materials for the synthesis of a wide number of different carbo-and heterocycles. The aim of this review is to give an overview of their utility in organic synthesis, highlighting the variety of compounds that can be directly accessed from single reactions over these systems. Thus, cycloaromatization processes are initially commented, followed by reactions directed towards the syntheses of five-membered rings, other carbocycles and, finally, heterocycles. The diverse methodologies that have been developed for the synthesis of each of these types of compounds from 1,3-dien-5-ynes are presented, emphasizing the influence of the reaction conditions and the use of additional reagents in the outcome of the transformations.2

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“…Compared to traditional convergent synthesis, divergent synthesis can generate molecule libraries with a high level of structural diversity in an efficient manner, which is of great importance in modern organic synthesis and drug discovery 1. Although recent years have witnessed significant achievements in this field,2 the development of a new strategy to achieve divergent synthesis with high chemo- and site-selectivity is still highly desirable.…”

mentioning

confidence: 99%

Ligand and counteranion enabled regiodivergent C–H bond functionalization of naphthols with α-aryl-α-diazoesters

Zhang

et al. 2019

Chem. Sci.

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Selectivity Control in Lewis Acid Catalyzed Regiodivergent Tandem Cationic Cyclization/Ring Expansion Terminated by Pinacol Rearrangement

Abstract: Catalyst is key: The title reaction sequence has been carried out on 1 in the presence of AgSbF6 (5 mol %) in DCE or In(OTf)3 (5 mol %) with MeOH (4 equiv) to afford 2 or 3, respectively, in up to >20:1 ratio (see scheme; DCE=1,2‐dichloroethane, Tf=trifluoromethanesulfonyl).

Cited by 77 publications

References 52 publications

Regio‐ and Site‐selective Molecular Rearrangements by Homogeneous Gold Catalysis

Regio‐ and Site‐selective Molecular Rearrangements by Homogeneous Gold Catalysis

1,3-Dien-5-ynes: Versatile Building Blocks for the Synthesis of Carbo- and Heterocycles

Ligand and counteranion enabled regiodivergent C–H bond functionalization of naphthols with α-aryl-α-diazoesters

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