Use of Triethylsilane for Directed Enantioselective Reduction of Olefines: Synthesis of Pyrazino[2,1‐<i>c</i>][1,4]oxazine‐6,9‐diones with Full Control of the Absolute Configuration

Ručilová, Veronika; Maloň, Michal; Soural, Miroslav

doi:10.1002/ejoc.201701553

Cited by 5 publications

(1 citation statement)

References 56 publications

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“…Importantly, the developed protocols and corresponding intermediates can be applied for the synthesis of differently fused 1,4-oxazepanes based on previously reported approaches targeted to fused morpholines. [27][28][29][30] Experimental section…”

Section: Discussionmentioning

confidence: 99%

Synthesis of chiral 1,4-oxazepane-5-carboxylic acids from polymer-supported homoserine

et al. 2020

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Section: Discussionmentioning

confidence: 99%

Synthesis of chiral 1,4-oxazepane-5-carboxylic acids from polymer-supported homoserine

et al. 2020

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A One-Pot Reaction of α-Imino Rhodium Carbenoids and Halohydrins: Access to 2,6-Substituted Dihydro-2H-1,4-oxazines

et al. 2020

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Herein, we report a Rh(II)-catalyzed reaction between 1-tosyl-1,2,3-triazoles and halohydrins to provide 2,6-substituted 3,4-dihydro-2H-1,4-oxazines under basic conditions. The reaction is proposed to undergo a rhodium carbenoid 1,3-insertion into O–H followed by an annulation. The scope includes phenyl or alkenyl C4-substituted triazoles and a range of halohydrins using catalytic Rh2Oct4 and K2CO3. A synthesis of the antimicrobial natural product (±)-chelonin C is also reported using this novel methodology.

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Synthesis of 2-Alkylsulfonyl-imidazoles with Three Diversity Positions from Immobilized α-Acylamino Ketones

Králová

Soural

2018

ACS Comb. Sci.

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The synthesis of novel imidazole derivatives via immobilized α-acylamino ketones is reported in this article. The key intermediates were prepared from the Wang-piperazine resin-supported Fmoc-amino acids. After their sulfonylation with 4-nitrobenzenesulfonyl chloride (4-Nos-Cl), followed by alkylation with α-bromoketones and cleavage of Nos group, the resulting α-acylamino ketones were reacted with Fmoc-isothiocyanate. The corresponding Fmoc-thioureas were subjected to the Fmoc-cleavage and spontaneous ring-closure to imidazole scaffold. The resulting imidazole-thiones were alkylated with alkyl halides and oxidized using meta-chloroperbenzoic acid ( mCPBA). Trifluoroacetic acid (TFA)-mediated cleavage yielded the corresponding trisubstituted 2-alkylsulfonyl imidazoles in good crude purity and acceptable overall yields. In the case of sulfides, prepared from alkyl bromides, the unexpected products brominated at the C position of the imidazole were obtained.

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Use of Triethylsilane for Directed Enantioselective Reduction of Olefines: Synthesis of Pyrazino[2,1‐c][1,4]oxazine‐6,9‐diones with Full Control of the Absolute Configuration

Cited by 5 publications

References 56 publications

Synthesis of chiral 1,4-oxazepane-5-carboxylic acids from polymer-supported homoserine

Synthesis of chiral 1,4-oxazepane-5-carboxylic acids from polymer-supported homoserine

A One-Pot Reaction of α-Imino Rhodium Carbenoids and Halohydrins: Access to 2,6-Substituted Dihydro-2H-1,4-oxazines

Synthesis of 2-Alkylsulfonyl-imidazoles with Three Diversity Positions from Immobilized α-Acylamino Ketones

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