Triethyloxonium Tetrafluoroborate

Perst, H.; Seapy, Dave G.

doi:10.1002/047084289x.rt223.pub2

Cited by 5 publications

(3 citation statements)

References 86 publications

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“…[23] The reduction of the tertiary amide obtained by N-methylation of 5 a.a was achieved via sequential treatment of the latter with Meerwein salt and sodium borohydride. [24] Under these conditions, fragmentation was observed in addition to reduction, and acyclic benzylamine 9 was formed in moderate yield. The completely saturated azepane 10 was obtained by reduction of 8 with LiAlH 4 .…”

Section: Methodsmentioning

confidence: 97%

“…Alternatively, the complete decarboxylation of 6 was achieved under Barton conditions to give lactam 8 [23] . The reduction of the tertiary amide obtained by N‐methylation of 5 a.a was achieved via sequential treatment of the latter with Meerwein salt and sodium borohydride [24] . Under these conditions, fragmentation was observed in addition to reduction, and acyclic benzylamine 9 was formed in moderate yield.…”

Section: Methodsmentioning

confidence: 99%

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(4+3) Annulation of Donor‐Acceptor Cyclopropanes and Azadienes: Highly Stereoselective Synthesis of Azepanones

Nicolai

Waser

2022

Angew Chem Int Ed

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Azepanes are important seven-membered heterocycles, which are present in numerous natural and synthetic compounds. However, the development of convergent synthetic methods to access them remains challenging. Herein, we report the Lewis acid catalyzed (4+3) annulative addition of aryl and amino donoracceptor cyclopropanes with 2-aza-1,3-dienes. Densely substituted azepane derivatives were obtained in good to excellent yields and with high diastereoselectivity. The reaction occurred under mild conditions with ytterbium triflate as the catalyst. The use of copper triflate with a trisoxazoline (Tox) ligand led to an enantioselective transformation. The obtained cycloadducts were convenient substrates for a series of further modifications, showing the synthetic utility of these compounds.

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Section: Methodsmentioning

confidence: 97%

Section: Methodsmentioning

confidence: 99%

(4+3) Annulation of Donor‐Acceptor Cyclopropanes and Azadienes: Highly Stereoselective Synthesis of Azepanones

Nicolai

Waser

2022

Angew Chem Int Ed

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“…Trimethyloxonium tetrafluoroborate (Me 3 OBF 4 ) and triethyloxonium tetrafluoroborate (Et 3 OBF 4 ), Meerwein's reagents, are widely used as alkylating agents of weak nucleophilic characteristic groups, like amides. [29] In 2004, the teams of Fuchs and Funk in the synthesis of the natural product (�)-Perophoramidine, when attempting to convert a lactam (cyclic amide) 61 to the corresponding cyclic imidate 62, successfully used Me 3 OBF 4 . In the case of this synthesis, DIPEA was used as base and dichloromethane was chosen as solvent.…”

Section: Synthesis From Amides or Lactamsmentioning

confidence: 99%

Synthetic Routes to Imidates and Their Applications in Organic Transformation: Recent Progress

Chaidali,

Lykakis

2023

Eur J Org Chem

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Recent synthetic approaches and diverse applications of imidates are presented in this review. These motifs are successfully used as intermediates in organic transformations, such as the synthesis of N‐heterocycles, natural products and metal complexes with a potential catalytic effect. Consequently, many attempts have been made for the development of efficient and facile synthetic methods of imidates in the past few years, as a continuum of previous paths. A wide range of organic compounds can be used as starting materials for these syntheses, including nitriles, isocyanides, amides etc. which through simple and flexible processes are converted to the desired imidates. Herein, an exploration of the recent synthetic routes of imidates and their diverse applications in organic transformations has been categorized and summarized.

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(4+3) Annulation of Donor‐Acceptor Cyclopropanes and Azadienes: Highly Stereoselective Synthesis of Azepanones

Nicolai

Waser

2022

Angewandte Chemie

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Triethyloxonium Tetrafluoroborate

Cited by 5 publications

References 86 publications

(4+3) Annulation of Donor‐Acceptor Cyclopropanes and Azadienes: Highly Stereoselective Synthesis of Azepanones

(4+3) Annulation of Donor‐Acceptor Cyclopropanes and Azadienes: Highly Stereoselective Synthesis of Azepanones

Synthetic Routes to Imidates and Their Applications in Organic Transformation: Recent Progress

(4+3) Annulation of Donor‐Acceptor Cyclopropanes and Azadienes: Highly Stereoselective Synthesis of Azepanones

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