Tandem Gold-Catalyzed Dehydrative Cyclization/Diels–Alder Reactions: Facile Access to Indolocarbazole Alkaloids

Borrero, Nicholas V.; DeRatt, Lindsey G.; Barbosa, Lais Ferreira; Abboud, Khalil A.; Aponick, Aaron

doi:10.1021/acs.orglett.5b00528

Cited by 30 publications

(10 citation statements)

References 56 publications

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“…The application of the Mo‐catalyzed reductive cyclization to the synthesis of complex molecules is exemplified in the preparation of the Boc‐protected Arcyriaflavin A, an indolocarbazole alkaloid. The synthetic sequence is reported in Scheme …”

Section: Use Of Molybdenum Catalysts With Phosphines or Glycols As Rementioning

confidence: 99%

“…The synthetic sequence is reported in Scheme 70. [196] The last step in the synthesis is the reductive cyclization of a nitro substituted intermediate. The authors reported that the cyclization to get the five-membered heterocycle could not be accomplished using the uncatalyzed Cadogan reaction, Grignard reagents or different amination methods.…”

Section: Synthesis Of Five-membered Ring Heterocycles Using Phosphinementioning

confidence: 99%

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Transition Metal Catalyzed Reductive Cyclization Reactions of Nitroarenes and Nitroalkenes

2019

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Nitroarenes are the entry point for the production of most nitrogen‐containing aromatic compounds. Thus, any transformation that leads directly from them to the final product allows saving one or more synthetic steps. This review deals with homogeneously catalyzed reactions leading to the formation of N‐heterocyclic compounds from nitroarenes or nitroalkenes in one pot. Reactions that lead to the intermediate formation of amines are not considered. Carbon monoxide is the most often employed reductant because it allows selective reactions, is cheap, and only produces CO2 as stoichiometric byproduct. However, the difficulty in handling pressurized CO has stimulated in recent years the development of CO‐surrogates, that is molecules able to liberate CO during the reaction. The use of phosphines and diols has also been developed in conjunction with molybdenum catalysts. The review focusses in more detail on the literature in the period 2006–2018, but reference to earlier work is made when necessary to put recent results in a more general context.

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Section: Use Of Molybdenum Catalysts With Phosphines or Glycols As Rementioning

confidence: 99%

Section: Synthesis Of Five-membered Ring Heterocycles Using Phosphinementioning

confidence: 99%

Transition Metal Catalyzed Reductive Cyclization Reactions of Nitroarenes and Nitroalkenes

2019

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“…Aponick and co‐workers made continuous efforts in gold‐catalyzed dehydrative cyclization of propargylic alcohols. In 2015, they reported a gold‐catalyzed synthesis of cyclic 2‐oxodienes from propargyl alcohols and the subsequent Diels−Alder reaction (Scheme ) . The dehydrative cyclization of the propargylic alcohol 65 generated diene 66 in situ in the presence of a gold catalyst, which then underwent cycloaddition with a variety of dienophiles.…”

Section: Gold‐catalyzed Transformation Of Propargyl Alcoholsmentioning

confidence: 99%

Gold‐Catalyzed Transformations of Propargyl Alcohols and Propargyl Amines

Zhang

Wang

2018

Asian J Org Chem

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“…By taking advantage of the presence of the diene, Diels–Alder cycloadditions were performed , . α‐Dienyl piperidine 2a was heated with diethyl but‐2‐ynedioate to give the corresponding Diels–Alder adduct 25 in a yield of 60 % .…”

Section: Resultsmentioning

confidence: 99%