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Review
. 2019 Feb 11;24(3):630.
doi: 10.3390/molecules24030630.

Stereoselective Multicomponent Reactions in the Synthesis or Transformations of Epoxides and Aziridines

Allan Ribeiro da Silva  1 , Deborah Araujo Dos Santos  2   3 , Marcio Weber Paixão  4 , Arlene Gonçalves Corrêa  5
Affiliations
Review

Stereoselective Multicomponent Reactions in the Synthesis or Transformations of Epoxides and Aziridines

Allan Ribeiro da Silva et al. Molecules. .

Abstract

Small ring heterocycles, such as epoxides and aziridines, are present in several natural products and are also highly versatile building blocks, frequently involved in the synthesis of numerous bioactive products and pharmaceuticals. Because of the potential for increased efficiency and selectivity, along with the advantages of environmentally benign synthetic procedures, multicomponent reactions (MCRs) have been explored in the synthesis and ring opening of these heterocyclic units. In this review, the recent advances in MCRs involving the synthesis and applications of epoxides and aziridines to the preparation of other heterocycles are discussed emphasizing the stereoselectivity of the reactions.

Keywords: asymmetric synthesis; aziridine; epoxides; green synthesis; multicomponent reactions.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Examples of natural products possessing epoxide and aziridine rings.
Scheme 1
Scheme 1
Total synthesis of (−)-indolizidine 223AB.
Scheme 2
Scheme 2
Three-component coupling involving aziridine, aryne, and aldehyde.
Scheme 3
Scheme 3
Proline-based chiral C3-symmetric organocatalyst for the synthesis of epoxide derivatives through a domino reaction.
Scheme 4
Scheme 4
Tandem asymmetric organocatalytic epoxidation/Passerini reaction.
Scheme 5
Scheme 5
Epoxide ring-opening multicomponent reaction catalyzed by Sq_IRMOF-16.
Scheme 6
Scheme 6
Asymmetric 3-CR and kinetic resolution of 1,3-oxazolidine derivatives.
Scheme 7
Scheme 7
Copper-catalyzed three-component linchpin coupling.
Scheme 8
Scheme 8
One-pot electrophilic aminoalkoxylation reaction.
Scheme 9
Scheme 9
Synthesis of trisubstituted morpholines through an electrophilic multicomponent reaction using epichlorohydrin, olefin, nosyl amide, and N-bromosuccinimide.
Scheme 10
Scheme 10
Formal synthesis of Carnitine acetyltransferase and Reboxetine.
Scheme 11
Scheme 11
Three-component synthesis of 1,3-oxazinane-2,4-diones catalyzed by the [(salph)Al(THF)2]+[Co(CO)4]− complex.
Scheme 12
Scheme 12
Cobalt-catalyzed 3-CR for the synthesis of 1,3-oxazinan-4-ones.
Scheme 13
Scheme 13
Palladium-catalyzed Catellani reaction using epoxides.
Scheme 14
Scheme 14
Three-component coupling of diethyl phosphite, α-ketoesters, and N-protected imines.
Scheme 15
Scheme 15
Multicomponent aziridination by BOROX catalysis.
Scheme 16
Scheme 16
Enantioselective multicomponent trans-aziridination of imines with diazo acetamides.
Scheme 17
Scheme 17
Protocol for the synthesis of 1,3-oxazolidines described by Majee and coworkers.
Scheme 18
Scheme 18
Aryne multicomponent coupling and use of aziridines as nucleophilic triggers.
Scheme 19
Scheme 19
Multicomponent approach for the synthesis of 1,2,4-oxadiazinane.
Scheme 20
Scheme 20
NBS-induced aminocyclization–aziridine ring expansion cascade of 70.
Scheme 21
Scheme 21
Palladium-catalyzed Catellani reaction for synthesis of tetrahydroisoquinolines.
Scheme 22
Scheme 22
Tandem three-component reactions between aziridines, arenes, and aldehydes.
Scheme 23
Scheme 23
Example of aziridine aldehyde dimer as an inducing group for building blocks synthesis.
Scheme 24
Scheme 24
Disrupted Ugi reaction with aziridine aldehyde dimers, isocyanides, and amino acids (or peptides).
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