Organocatalyzed Asymmetric Friedel‐Crafts Reactions: An Update

Heravi, Majid M.; Zadsirjan, Vahideh; Heydari, Masumeh; Masoumi, Baharak

doi:10.1002/tcr.201800190

Cited by 37 publications

(14 citation statements)

References 303 publications

(218 reference statements)

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“…Asymmetric Friedel-Crafts reaction is another widely used method for the enantioselective construction of carbon-carbon bonds [21]. The title transformation is often used in the synthesis of biologically active compounds [22] and some organocatalytic approaches have been compiled in a review article in 2019 [23]. Among the extremely wide variety of chiral sources used in asymmetric Friedel-Crafts reaction, in this review, special attention is paid to systems such as chiral derivatives of urea [24], thiourea [24], squaramide, chiral phosphoric acids and various complexes of N-heterocycles with metals.…”

Section: Asymmetric Friedel-crafts Reactionsmentioning

confidence: 99%

Recent Advances in Selected Asymmetric Reactions Promoted by Chiral Catalysts: Cyclopropanations, Friedel–Crafts, Mannich, Michael and Other Zinc-Mediated Processes—An Update

2021

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The main purpose of this review article is to present selected asymmetric synthesis reactions in which chemical and stereochemical outcomes are dependent on the use of an appropriate chiral catalyst. Optically pure or enantiomerically enriched products of such transformations may find further applications in various fields. Among an extremely wide variety of asymmetric reactions catalyzed by chiral systems, we are interested in: asymmetric cyclopropanation, Friedel–Crafts reaction, Mannich and Michael reaction, and other stereoselective processes conducted in the presence of zinc ions. This paper describes the achievements of the above-mentioned asymmetric transformations in the last three years. The choice of reactions is related to the research that has been carried out in our laboratory for many years.

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Section: Asymmetric Friedel-crafts Reactionsmentioning

confidence: 99%

Recent Advances in Selected Asymmetric Reactions Promoted by Chiral Catalysts: Cyclopropanations, Friedel–Crafts, Mannich, Michael and Other Zinc-Mediated Processes—An Update

2021

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“…α-Amidoalkylation reactions play an increasingly important role in organic synthesis as convenient and effective methods for the formation of C-C and C-heteroatom bonds, particularly of the intramolecular type, allowing the synthesis of carbo- or heterocyclic systems. In most cases, N -acylimine 2 or N -acyliminium cations 3 are the correct α-amidoalkylating agents and they are generated from precursors with the relevant structure 1 ( Scheme 1 ) [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 ].…”

Section: Introductionmentioning

confidence: 99%

1-Aminoalkylphosphonium Derivatives: Smart Synthetic Equivalents of N-Acyliminium-Type Cations, and Maybe Something More: A Review

et al. 2022

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N-acyliminium-type cations are examples of highly reactive intermediates that are willingly used in organic synthesis in intra- or intermolecular α-amidoalkylation reactions. They are usually generated in situ from their corresponding precursors in the presence of acidic catalysts (Brønsted or Lewis acids). In this context, 1-aminoalkyltriarylphosphonium derivatives deserve particular attention. The positively charged phosphonium moiety located in the immediate vicinity of the N-acyl group significantly facilitates Cα-P+ bond breaking, even without the use of catalyst. Moreover, minor structural modifications of 1-aminoalkyltriarylphosphonium derivatives make it possible to modulate their reactivity in a simple way. Therefore, these types of compounds can be considered as smart synthetic equivalents of N-acyliminium-type cations. This review intends to familiarize a wide audience with the unique properties of 1-aminoalkyltriarylphosphonium derivatives and encourage their wider use in organic synthesis. Hence, the most important methods for the preparation of 1-aminoalkyltriarylphosphonium salts, as well as the area of their potential synthetic utilization, are demonstrated. In particular, the structure–reactivity correlations for the phosphonium salts are discussed. It was shown that 1-aminoalkyltriarylphosphonium salts are not only an interesting alternative to other α-amidoalkylating agents but also can be used in such important transformations as the Wittig reaction or heterocyclizations. Finally, the prospects and limitations of their further applications in synthesis and medicinal chemistry were considered.

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“…A great interest has been arised to enhance these precious chiral structures to achieve remarkable results in asymmetric synthesis [1–5] . Countless studies have been done in many different types of reactions such as Michael, [5–9] aldol, [10–16] Diels‐Alder, [17–21] Henry, [22–27] aza‐Henry, [28–33] Friedel‐Crafts, [34–38] Povarov, [39–42] decarboxylative Doebner‐Knoevenagel [43,44] reactions and many others. Although asymmetric organocatalysis can be considered as the most successful and easy way to synthesize enantioenriched compounds, [45] one of the most debated drawbacks is the possibility of agglomeration and aggregation due to high catalyst loading in the reactions.…”

Section: Introductionmentioning

confidence: 99%