A highly adaptable catalyst/substrate system for the synthesis of substituted chromenes

Aponick, Aaron; Biannic, Bérenger; Jong, Michael R.

doi:10.1039/c0cc01961e

Cited by 64 publications

(22 citation statements)

References 36 publications

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“…15 Concurrent with our efforts, Bandini and Aponick have developed effective gold(I)-catalyzed methods for the intramolecular arylation 16 and alkoxylation 17 of allylic alcohols, and these results pointed to the feasibility of gold(I)-catalyzed intramolecular allylic amination. Furthermore, Aponick’s demonstration of gold(I)-catalyzed intramolecular amination of propargylic alcohols with secondary alkylamines suggested that alkylamines might also be suitable nucleophiles for gold(I)-catalyzed intramolecular allylic amination.…”

mentioning

confidence: 81%

Gold(I)-Catalyzed Intramolecular Amination of Allylic Alcohols With Alkylamines

Mukherjee

Widenhoefer

2011

Org. Lett.

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A 1:1 mixture of (1)AuCl [1 = P(t-Bu)2o-biphenyl] and AgSbF6 catalyzes the intramolecular amination of allylic alcohols with alkylamines to form substituted pyrrolidine and piperidine derivatives. Gold(I)-catalyzed cyclization of (R,Z)-8-(N-benzylamino)-3-octen-2-ol (96% ee, 95% de) led to isolation of (R,E)-1-benzyl-2-(1-propenyl)piperidine in 99% yield with 96% ee, consistent with the net syn addition of the amine relative to the departing hydroxyl group.

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confidence: 81%

Gold(I)-Catalyzed Intramolecular Amination of Allylic Alcohols With Alkylamines

Mukherjee

Widenhoefer

2011

Org. Lett.

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“…The reaction proceeds via an enamine intermediate 2. 13 2.14. Adler and Baldwin developed an efficient single-step method for the synthesis of 2,2-dimethyl-2H-chromenes from the corresponding phenols with 3-methylbutenal under microwave irradiation in CDCl 3 (Scheme 85).…”

Section: Acs Catalysismentioning

confidence: 98%

Catalytic Synthesis of 2H-Chromenes

et al. 2015

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2H-Chromenes (2H-1-benzopyran derivatives) display a broad spectrum of biological activities. The 2H-chromene substructure is an important structural motif present in a variety of medicines, natural products, and materials showing unique photophysical properties. Hence, the structural importance of the benzopyran moiety has elicited a great deal of interest in the field of organic synthesis and chemical biology to develop new and improved synthesis of these molecular skeletons. This review gives an up-to-date overview of different catalytic methodologies developed for the synthesis of 2H-chromenes and is structured around the three main approaches applied in catalytic 2H-chromene synthesis: (I) catalysis with (transition) metals, (II) metal-free Brønsted and Lewis acid/base catalysis, which includes examples of nonenantioselective organocatalysis, and (III) enantioselective organo-catalysis. The section in which the metal-catalyzed reactions are discussed describes different ring-closing strategies based on (transition) metal catalysis, including a few enantioselective approaches. For most of these reactions, plausible mechanisms are delineated. Moreover, synthesis of some natural products and medicinally important drugs are included. Specific advantages and disadvantages of the several synthetic methodologies are discussed. The review focuses on catalytic 2H-chromene synthesis. However, for a complete overview, synthetic routes involving some stoichiometric steps and reactions producing ring-scaffolds that are closely related to 2H-chromenes are also included.

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“…[9] Regarding the formation of carbon–oxygen bonds, Pd II , [10] Au I , [11-16] and Ru II [17] complexes catalyze the intramolecular dehydrative alkoxylation of allylic alcohols with simple alcohol nucleophiles. Conversely, the intermolecular alkoxylation of underivatized allylic alcohols remains an unsolved challenge in homogeneous catalysis.…”

Section: Introductionmentioning

confidence: 99%

The Regio‐ and Stereospecific Intermolecular Dehydrative Alkoxylation of Allylic Alcohols Catalyzed by a Gold(I) N‐Heterocyclic Carbene Complex

Mukherjee

Widenhoefer

2013

Chemistry A European J

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A 1:1 mixture of (IPr)AuCl [IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidine] and AgClO4 catalyzes the intermolecular dehydrative alkoxylation of primary and secondary allylic alcohols with aliphatic primary and secondary alcohols to form allylic ethers. These transformations are regio- and stereospecific with preferential addition of the alcohol nucleophile at the γ-position of the allylic alcohol syn to the departing hydroxyl group and with predominant formation of the E stereoisomer. The minor α-regioisomer is formed predominantly through a secondary reaction manifold involving regioselective γ-alkoxylation of the initially formed allylic ether rather than via the direct α-alkoxylation of the allylic alcohol.

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A highly adaptable catalyst/substrate system for the synthesis of substituted chromenes

Cited by 64 publications

References 36 publications

Gold(I)-Catalyzed Intramolecular Amination of Allylic Alcohols With Alkylamines

Gold(I)-Catalyzed Intramolecular Amination of Allylic Alcohols With Alkylamines

Catalytic Synthesis of 2H-Chromenes

The Regio‐ and Stereospecific Intermolecular Dehydrative Alkoxylation of Allylic Alcohols Catalyzed by a Gold(I) N‐Heterocyclic Carbene Complex

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