NbCl5: A Novel Lewis Acid in Allylation Reactions

Andrade, Carlos Kleber Z.; Azevedo, Neucírio Ricardo de; Oliveira, Guilherme R.

doi:10.1055/s-2002-28504

Cited by 27 publications

(8 citation statements)

References 11 publications

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“…Instead of addition of the appropriate enol ether, in these cases allyl phenyl ether (12; 2 mmol) was used. Analytical data for compounds 13 e, [18] 13 f, [19] 13 g, [20] and 13 h [21] were in complete accordance with literature values. 2 mmol).…”

Section: Methodssupporting

confidence: 83%

Zirconium‐Mediated Coupling Reactions of Amines and Enol or Allyl Ethers: Synthesis of Allyl‐ and Homoallylamines

Barluenga

Rodríguez

Alvarez‐Rodrigo

et al. 2003

Chemistry A European J

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An easy and efficient zirconium-mediated synthesis of allylamines from simple amines and enol ethers is described. This strategy also allows the synthesis of amino alcohol derivatives containing a Z double bond in their structure when 2,3-dihydrofuran is used. Simple conventional modification of these amino alcohols leads to 2-substituted piperidine derivatives. By applying this approach, a formal total synthesis of the alkaloid coniine is easily achieved from a protected butylamine. Finally, the zirconium-mediated reaction of amines and allyl phenyl ether furnishes homoallylamines or amino ethers depending on the structure of the starting amine.

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Section: Methodssupporting

confidence: 83%

Zirconium‐Mediated Coupling Reactions of Amines and Enol or Allyl Ethers: Synthesis of Allyl‐ and Homoallylamines

Barluenga

Rodríguez

Alvarez‐Rodrigo

et al. 2003

Chemistry A European J

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“…7 We wish to report that citronellal undergoes cyclization in the presence of catalytic amounts of NbCl 5 , TaCl 5 and InCl 3 . 8 NbCl 5 has been successfully used in our group as Lewis acid in a variety of reactions 9 and has gained increasing attention in recent years. 10 We decided to test TaCl 5 for comparison since niobium and tantalum belong to the same family in the periodic table.…”

Section: Introductionmentioning

confidence: 99%

Intramolecular ene reactions catalyzed by NbCl5, TaCl5 and InCl3

Andrade¹,

Vercillo²,

Rodrigues³

et al. 2004

J. Braz. Chem. Soc.

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Niobium pentachloride, tantalum pentachloride and indium trichloride efficiently catalysed the cyclization of (R)-citronellal to a mixture of isopulegol and neoisopulegol in good yields. A comparative study was carried out which demonstrated that NbCl 5 is the most active Lewis acid whereas InCl 3 is the most selective one. The selectivity of the reactions varied according to the Lewis acid used and to the solvent. The ene reaction of a 1,7-diene was also investigated. In this case, all Lewis acids tested showed excellent selectivity.

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“…For example, they are known to react with carbon-nitrogen, [1,2] carbon-oxygen [3,4] and carboncarbon multiple bonds [5,6] to give 1,2-dianion or radical species. On the other hand, recent studies of Nb V have focused on organic transformations in carbon-carbon bond formation which are typical Lewis acid-mediated reactions, [7][8][9] except for unique reactions such as cyclopropane formation [10] and dealkylative acylation. [11] We were interested in the strong Lewis acidity of Nb V , and started to investigate its unique reactivity.…”

Section: Introductionmentioning

confidence: 99%