Enantiomerically Pure Cyclopropylamines from Cyclopropylboronic Esters

Pietruszka, Jörg; Solduga, Gemma

doi:10.1002/ejoc.200900882

Cited by 39 publications

(18 citation statements)

References 101 publications

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“…For example, Pd(OAc) 2 -catalyzed reaction of compound 18 with diazomethane gave a mixture of cyclopropanes 19a and 19b as a separable 1:1 mixture (Scheme 6). 37 Utility of the method was demonstrated by employing it as a key step in the syntheses of biologically active products -belactosin A and tranylcypromine.…”

Section: Scheme 5 Stereocontrolled Cyclopropanation Of Alkenyl Boronamentioning

confidence: 99%

Cycloadditions of Alkenylboronic Derivatives

et al. 2020

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The literature on cycloaddition reactions of boron-containing alkenes is surveyed with 132 references. The data are categorized according to the reaction type ([2+1], [2+2], [3+2], [4+2], and [4+3] cycloadditions). The cyclopropanation and the Diels–Alder reactions of alkenylboronic derivatives have been studied more or less comprehensively, and for some substrates, they can be considered as convenient methods for the rapid regio- and stereoselective construction of even complex cyclic systems. Other types of the cycloadditions, as well as mechanistic aspects of the processes, have been addressed less thoroughly in the previous works.1 Introduction2 [2+1] Cycloaddition2.1 Cyclopropanation2.1.1 With Methylene Synthetic Equivalents2.1.2 With Substituted Carbenoids2.2 Epoxidation2.3 Aziridination3 [2+2] Cycloaddition4 [3+2] Cycloaddition4.1 With Nitrile Oxides4.2 With Diazoalkanes4.3 With Nitrones4.4 With Azomethine Ylides5 [4+2] Cycloaddition6 [4+3] Cycloaddition7 Conclusions and Outlook

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Section: Scheme 5 Stereocontrolled Cyclopropanation Of Alkenyl Boronamentioning

confidence: 99%

Cycloadditions of Alkenylboronic Derivatives

et al. 2020

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“…3 The spectral data matched with those reported in the literature. 5 2-(Azidomethyl)pyridine (11e). NaN3 (11.8 g, 181.6 mmol) and 2chloromethylpyridine hydrochloride (5.7 g, 45.1 mmol) were added to 200 mL of deionised water.…”

Section: -(3-azidopropyl)benzene (11a)mentioning

confidence: 99%

Synthesis and Spectral Properties of 6'-Triazolyl-Dihydroxanthene-Hemicyanine Fused Near-Infrared Dyes

Li¹,

Renault²,

Romieu

et al. 2020

Preprint

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We describe the synthesis of a range of 6’-triazolyl-dihydroxanthene-hemicyanine (DHX-hemicyanine) fused dyes through an effective copper-catalyzed azide-alkyne cycloaddition (CuAAC) "click" reaction, with the dual aim of providing molecular diversity and fine tuning spectral properties of these near-infrared (NIR)-active materials. This was implemented by reacting 16 different aliphatic and aromatic azides with a terminal alkynyl-based-DHX-hemicyanine hybrid scaffold prepared in four steps and 35% overall yield from 4-bromosalicylaldehyde. The resulting triazole derivatives have been fully characterized and their optical properties determined both in organic solvents and simulated physiological conditions (phosphate buffered saline containing 5% of bovine serum albumin protein). This systematic study is a first important step towards the development of NIR-I fluorogenic "click-on" dyes or related photoactive agents for light-based diagnostic and/or therapeutic applications.

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“…This method involved mixing a potassium organotrifluoroborate with SiCl 4 in the presence of allyl azide to generate the N-substituted allyl amine. 148,149 Other reactions using allyl azide are known, but will not be discussed further. [150][151][152][153][154][155][156] It is worth noting that low molecular weight azides, such as this one, are potentially explosive.…”

Section: Allyl Azidementioning

confidence: 99%