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Review
. 2021 Sep 13;22(18):9861.
doi: 10.3390/ijms22189861.

3-Arylaziridine-2-carboxylic Acid Derivatives and (3-Arylaziridin-2-yl)ketones: The Aziridination Approaches

Boriss Strumfs  1   2 , Romans Uljanovs  2 , Kirils Velikijs  2 , Peteris Trapencieris  1 , Ilze Strumfa  2
Affiliations
Review

3-Arylaziridine-2-carboxylic Acid Derivatives and (3-Arylaziridin-2-yl)ketones: The Aziridination Approaches

Boriss Strumfs et al. Int J Mol Sci. .

Abstract

Aziridination reactions represent a powerful tool in aziridine synthesis. Significant progress has been achieved in this field in the last decades, whereas highly functionalized aziridines including 3-arylated aziridine-2-carbonyl compounds play an important role in both medical and synthetic chemistry. For the reasons listed, in the current review we have focused on the ways to obtain 3-arylated aziridines and on the recent advances (mainly since the year 2000) in the methodology of the synthesis of these compounds via aziridination.

Keywords: aziridination; aziridines; carbenes; imines; nitrenes.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
The general pathways of aziridination. (A) carbon insertion in the imine double bond via carbene sources; (B) ni-trogen insertion in the olefin double bond via nitrene sources
Scheme 2
Scheme 2
Wulff’s type aziridination (AZ reaction) [10,11,12,13,14,15,16,17,18,19,20,21,22,23,24,25,26,27,28,29,31,32].
Scheme 3
Scheme 3
Aryl ligands for Wulff’s aziridination [10,11,12,13,14,27,28].
Scheme 4
Scheme 4
Boroxinate catalyst [15,17,21].
Scheme 5
Scheme 5
Boroxinate and BINOL catalysts in AZ reaction [29,30,31,32,33,34,35,36].
Scheme 6
Scheme 6
AZ reaction with Maruoka’s catalysts [33].
Scheme 7
Scheme 7
Ruthenium catalysts for the AZ reaction [37,38,39].
Scheme 8
Scheme 8
Aziridination with a chiral diazonium reagent [42,43].
Scheme 9
Scheme 9
Synthesis of 3-arylaziridine ketoesters [44].
Scheme 10
Scheme 10
Lewis acid-catalyzed aziridination [47].
Scheme 11
Scheme 11
Pyridinium triflate-catalyzed aziridination products [56].
Scheme 12
Scheme 12
Sweeney’s aza-Darzen type aziridination [58,59].
Scheme 13
Scheme 13
aza-Darzen aziridinations with chiral imines [60,61,62,63,64].
Scheme 14
Scheme 14
Spirocyclic aziridine products via aza-Darzen aziridination [65].
Scheme 15
Scheme 15
Diketones and diesters in aza-Darzen aziridination [66,67,68,69].
Scheme 16
Scheme 16
Reformatsky type aza-Darzen aziridination [70].
Scheme 17
Scheme 17
Cascade aziridination examples [71].
Scheme 18
Scheme 18
Ishikava’s aziridination [72,73,74,75,76,77].
Scheme 19
Scheme 19
DABCO-promoted aziridination [78].
Scheme 20
Scheme 20
Ammonium salt-promoted aziridination via ylides [79].
Scheme 21
Scheme 21
Aziridination with chiral stabilized trimethylammonium salt [80].
Scheme 22
Scheme 22
Aggarwal’s aziridination [81,82].
Scheme 23
Scheme 23
Sulfur ylide aziridination [82].
Scheme 24
Scheme 24
Sulfur ylide aziridination products [83,84].
Scheme 25
Scheme 25
Benzyne-promoted Darzen-type aziridination [85].
Scheme 26
Scheme 26
Evans aziridination [86,87,88,89].
Scheme 27
Scheme 27
Chiral ligands for Evans aziridination [90,91,92,95].
Scheme 28
Scheme 28
AnBOX and cHBOX ligands [95,96,97].
Scheme 29
Scheme 29
Oxidative aziridination of a chiral substrate [104].
Scheme 30
Scheme 30
Oxidative aziridination using a chiral ligand [106].
Scheme 31
Scheme 31
Iodobenzene diacetate-promoted oxidative aziridination [111].
Scheme 32
Scheme 32
Yudin’s modification of oxidative aziridination [113].
Scheme 33
Scheme 33
An example of a highly functionalized product of oxidative aziridination [116].
Scheme 34
Scheme 34
Sodium 2-iodoxybenzoate-promoted oxidative aziridination [117].
Scheme 35
Scheme 35
QNOAc-promoted aziridination [118].
Scheme 36
Scheme 36
The product of intramolecular aziridination [119].
Scheme 37
Scheme 37
EnH-NH2-promoted oxidative aziridination [120].
Scheme 38
Scheme 38
1-Aminopyridinium iodide as the nitrogen source in aziridination [121].
Scheme 39
Scheme 39
Anilines as the nitrogen source in oxidative aziridination [122].
Scheme 40
Scheme 40
Oxaziridine-promoted oxidative aziridination [124].
Scheme 41
Scheme 41
N,N-dihalogene-p-toluenesulfonamides as the nitrogen source in aziridination [125,126,127].
Scheme 42
Scheme 42
An example of N-sulfenylaziridine product [129].
Scheme 43
Scheme 43
Michael-type addition-based aziridination [131].
Scheme 44
Scheme 44
Carbamate reagent-based aziridination products [132,133].
Scheme 45
Scheme 45
Asymmetric organocatalytic aziridination of enones with carbamate reagent [134].
Scheme 46
Scheme 46
Enantioselective organocatalytic aziridination of α,β–unsaturated aldehydes [135].
Scheme 47
Scheme 47
Hydroxylamine reagent-mediated aziridination products [137,138].
Scheme 48
Scheme 48
Armstrong’s aziridination [139,140,141].
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