Straightforward Synthesis of Bridged Azaoxa Skeletons: Gold‐Catalyzed Aminoketalization of Garner’s Aldehyde‐Derived Alkynes

Alcaide, Benito; Almendros, Pedro; Carrascosa, Rocío

doi:10.1002/chem.201100139

Cited by 47 publications

(17 citation statements)

References 42 publications

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“…Decreasing temperature, while increasing the catalyst loading and the amount of nucleophile, led selectively after 4 days to aminal 3 in good yield. 18 Monitoring the reaction by 1 H NMR allowed to detect the corresponding fivemembered methylene sultam, which was clearly the intermediate of the aminal 3 (See supporting information). The favored 5-exo-dig pathway at lower temperature is consistent with the known cyclization of terminal alkynes 19 and with the involvement of a σ,π-digold acetylide complex in the mechanism.…”

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confidence: 99%

Benzosultam Synthesis by Gold(I)-Catalyzed Ammonium Formation/Nucleophilic Substitution

et al. 2019

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The synthesis of benzosultams has been achieved through a gold(I)-catalyzed ammonium formation strategy. Starting from easily available N-(2-alkynyl)phenylsulfonyl azetidine derivatives, a cyclization reaction generated a spiroammonium gold intermediate which was ring-opened by nucleophilic alcohol or indole. This new methodology is compatible with large variation on the substrates and nucleophiles, and allowed to form benzosultams in high yield (18-98%, 20 examples). This strategy also allowed the preparation of benzosultam analogs via iododeauration and subsequent cross-coupling reactions.

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confidence: 99%

Benzosultam Synthesis by Gold(I)-Catalyzed Ammonium Formation/Nucleophilic Substitution

et al. 2019

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“…The alkynyl-β-lactams by direct bisheterocyclization afforded optically pure tricyclic bridged acetals containing a 2-azetidinone nucleus with regiocontrolled Au/ Bronsted acid co-catalyst [266,267]. The desired ketal was produced when terminal alkyne was treated with gold(III) chloride/p-toluenesulfonic acid catalytic system.…”

Section: Synthesis Of Six-membered Oxygen and Nitrogen Containing Hetmentioning

confidence: 99%

Gold-catalyzed C–O bond forming reactions for the synthesis of six-membered O-heterocycles

et al. 2019

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The heterocycles are present in the drugs and pesticides in a major proportion and development of new strategies for the synthesis of these compounds is attractive topic for the synthetic and medicinal chemists. Synthesis of heterocycles is one of the important areas in synthetic organic chemistry. The present manuscript reported the synthesis of six-membered heterocylces with oxygen heteroatom using gold catalysts. This review covered interesting discoveries in the past few years.

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“…Regiocontrolled gold/Brønsted acid co-catalyzed direct bis-heterocyclization of alkynyl-β-lactams allows the efficient synthesis of optically pure tricyclic bridged acetals bearing a 2-azetidinone nucleus [ 66 – 67 ]. Treatment of the terminal alkyne 35a with the catalytic system AuCl 3 /PTSA gave the desired ketal 36a .…”

Section: Reviewmentioning

confidence: 99%

Gold-catalyzed heterocyclizations in alkynyl- and allenyl-β-lactams

Alcaide¹,

Almendros

2011

Beilstein J. Org. Chem.

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Straightforward Synthesis of Bridged Azaoxa Skeletons: Gold‐Catalyzed Aminoketalization of Garner’s Aldehyde‐Derived Alkynes

Cited by 47 publications

References 42 publications

Benzosultam Synthesis by Gold(I)-Catalyzed Ammonium Formation/Nucleophilic Substitution

Benzosultam Synthesis by Gold(I)-Catalyzed Ammonium Formation/Nucleophilic Substitution

Gold-catalyzed C–O bond forming reactions for the synthesis of six-membered O-heterocycles

Gold-catalyzed heterocyclizations in alkynyl- and allenyl-β-lactams

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