Use of chiral auxiliaries in the asymmetric synthesis of biologically active compounds: A review

Díaz, Gaspar; Miranda, Izabel Luzia; Sartori, Suélen K.; Rezende, Daniele Cristina de; Diaz, Marisa Alves Nogueira

doi:10.1002/chir.23103

Cited by 61 publications

(36 citation statements)

References 176 publications

(231 reference statements)

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“…chiral auxiliary induced chirality strategy because the carboxylate can be served as a handle for the incorporation of a chiral auxiliary 63 . However, they are rarely employed in radical processes 64,65 probably because of the high reactivity of radial species.…”

Section: Resultsmentioning

confidence: 99%

Organophotocatalytic dearomatization of indoles, pyrroles and benzo(thio)furans via a Giese-type transformation

Zhang

Gao

et al. 2021

Commun Chem

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Accessing fascinating organic and biological significant indolines via dearomatization of indoles represents one of the most efficient approaches. However, it has been difficult for the dearomatization of the electron deficient indoles. Here we report the studies leading to developing a photoredox mediated Giese-type transformation strategy for the dearomatization of the indoles. The reaction has been implemented for chemoselectively breaking indolyl C=C bonds embedded in the aromatic system. The synthetic power of this strategy has been demonstrated by using structurally diverse indoles bearing common electron-withdrawing groups including (thio)ester, amide, ketone, nitrile and even aromatics at either C2 or C3 positions and ubiquitous carboxylic acids as radical coupling partner with high trans-stereoselectivity (>20:1 dr). This manifold can also be applied to other aromatic heterocycles including pyrroles, benzofurans and benzothiophenes. Furthermore, enantioselective dearomatization of indoles has been achieved by a chiral camphorsultam auxiliary with high diastereoselectivity.

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Section: Resultsmentioning

confidence: 99%

Organophotocatalytic dearomatization of indoles, pyrroles and benzo(thio)furans via a Giese-type transformation

Zhang

Gao

et al. 2021

Commun Chem

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“…A final and more novel approach can be seen in a 2005 paper published by Mendoza that discloses access to N ‐substituted TZD structures derived from oxazolidinethiones [23] . Chiral auxiliaries have been used to construct bioactive compounds [24] . The chiral auxiliary used in Mendoza‘s work can be seen as a derivative of the renowned Evans auxiliary ( 18 ), with the only difference being a replacement of the carbonyl function to a thione ( 19 ).…”

Section: Substitution Reactionsmentioning

confidence: 99%

Thiazolidinediones: An In–Depth Study of Their Synthesis and Application to Medicinal Chemistry in the Treatment of Diabetes Mellitus

2021

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2,4‐Thiazolidinedione (TZD) is a privileged and highly utilised scaffold for the development of pharmaceutically active compounds. This sulfur‐containing heterocycle is a versatile pharmacophore that confers a diverse range of pharmacological activities. TZD has been shown to exhibit biological action towards a vast range of targets interesting to medicinal chemists. In this review, we attempt to provide insight into both the historical conventional and the use of novel methodologies to synthesise the TZD core framework. Further to this, synthetic procedures utilised to substitute the TZD molecule at the activated methylene C5 and N3 position are reviewed. Finally, research into developing clinical agents, which act as modulators of peroxisome proliferator‐activated receptors gamma (PPARγ), protein tyrosine phosphatase 1B (PTP1B) and aldose reductase 2 (ALR2), are discussed. These are the three most targeted receptors for the treatment of diabetes mellitus (DM).

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“…Zakarian et al reported direct methylation of ( S )-naproxen using a chiral enolate, as shown in Scheme 17 . In contrast to conventional chiral alkylation requiring chiral auxiliary attachment and detachment [ 62 , 63 ], this chiral enolate (reagent) gives the desired product directly in a highly stereoselective manner. Although the author reported that the recovery of chiral amines was possible and readily available [ 64 ], excess use of base and electrophile needs to be improved for further application and industrial-scale synthesis.…”

Section: Recent Synthetic Advances In Naproxenmentioning

confidence: 99%

Recent Advances in the Synthesis of Ibuprofen and Naproxen

Paek

2021

Molecules

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Herein, we review the recent progress in the synthesis of representative nonsteroidal anti-inflammatory drugs (NSAIDs), ibuprofen and naproxen. Although these drugs were discovered over 50 years ago, novel practical and asymmetric approaches are still being developed for their synthesis. In addition, this endeavor has enabled access to more potent and selective derivatives from the key frameworks of ibuprofen and naproxen. The development of a synthetic route to ibuprofen and naproxen over the last 10 years is summarized, including developing methodologies, finding novel synthetic routes, and applying continuous-flow chemistry.

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Use of chiral auxiliaries in the asymmetric synthesis of biologically active compounds: A review

Cited by 61 publications

References 176 publications

Organophotocatalytic dearomatization of indoles, pyrroles and benzo(thio)furans via a Giese-type transformation

Organophotocatalytic dearomatization of indoles, pyrroles and benzo(thio)furans via a Giese-type transformation

Thiazolidinediones: An In–Depth Study of Their Synthesis and Application to Medicinal Chemistry in the Treatment of Diabetes Mellitus

Recent Advances in the Synthesis of Ibuprofen and Naproxen

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