Organocatalytic Transfer Hydrogenation and Hydrosilylation Reactions

Herrera, Raquel P.

doi:10.1007/s41061-016-0032-4

Cited by 23 publications

(12 citation statements)

References 226 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thus, the catalyst role was mainly analyzed through the observed enantioselectivity. The low degree of induction achieved with Cbz-L-Val was surprising, since a variety of catalysts have been reported based on this amino acid [4][5][6][7][47][48][49]. Only appreciable asymmetric induction (62% ee) was observed for Cbz-L-Pro, probably due to its cyclic structure that can reduce the conformational freedom at the transition state, favoring an efficient chirality transfer [50].…”

Section: Catalyst Screeningmentioning

confidence: 99%

“…In this context, the asymmetric transfer hydrogenation of imines represents a simple and attractive approach to target the synthesis of enantiopure amines, and a variety of catalytic methodologies have been developed for this purpose [4][5][6][7][8][9][10][11][12]. The use of trichlorosilane and related reagents for this purpose has attracted much attention in recent years, having shown their capacity for the transfer hydrogenation of a variety of groups, such imines [4][5][6][7][8][9][10][11][12], enones [13,14], nitro groups [15,16], and N-heteroarenes [17,18], in the synthesis of substituted hydrazines [19], and in the reduction of CO 2 in the presence of amines [20][21][22][23]. Thus, the organocatalytic reduction of ketimines with trichlorosilane provides an efficient methodology for the asymmetric preparation of amines [24][25][26].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Rational Design of Simple Organocatalysts for the HSiCl3 Enantioselective Reduction of (E)-N-(1-Phenylethylidene)aniline

et al. 2021

View full text Add to dashboard Cite

Prolinamides are well-known organocatalysts for the HSiCl3 reduction of imines; however, custom design of catalysts is based on trial-and-error experiments. In this work, we have used a combination of computational calculations and experimental work, including kinetic analyses, to properly understand this process and to design optimized catalysts for the benchmark (E)-N-(1-phenylethylidene)aniline. The best results have been obtained with the amide derived from 4-methoxyaniline and the N-pivaloyl protected proline, for which the catalyzed process is almost 600 times faster than the uncatalyzed one. Mechanistic studies reveal that the formation of the component supramolecular complex catalyst-HSiCl3-substrate, involving hydrogen bonding breaking and costly conformational changes in the prolinamide, is an important step in the overall process.

show abstract

Section: Catalyst Screeningmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Rational Design of Simple Organocatalysts for the HSiCl3 Enantioselective Reduction of (E)-N-(1-Phenylethylidene)aniline

et al. 2021

View full text Add to dashboard Cite

show abstract

“…[191] Other small-molecule ARVs in development as microbicides include the NNRTI UC781, [192] several protease inhibitors (PIs, including SQV, darunavir [DRV], lopinavir [LPV], and RTV) [193] and several integrase inhibitors (IIs, including RAL, EVG, and L-870 812). [194] Presentation of clinical studies involving these compounds is given in the proceeding sections for the particular formulation formats in which they have been tested.…”

Section: Topical Prepmentioning

confidence: 99%

Pharmaceutical Approaches to HIV Treatment and Prevention

Yavuz

Morgan

Showalter

et al. 2018

Advanced Therapeutics

View full text Add to dashboard Cite

Human immunodeficiency virus (HIV) infection continues to pose a major infectious disease threat worldwide. It is characterized by the depletion of CD4 + T cells, persistent immune activation, and increased susceptibility to secondary infections. Advances in the development of antiretroviral drugs and combination antiretroviral therapy have resulted in a remarkable reduction in HIV-associated morbidity and mortality. Antiretroviral therapy (ART) leads to effective suppression of HIV replication with partial recovery of host immune system and has successfully transformed HIV infection from a fatal disease to a chronic condition. Additionally, antiretroviral drugs have shown promise for prevention in HIV pre-exposure prophylaxis and treatment as prevention. However, ART is unable to cure HIV. Other limitations include drug-drug interactions, drug resistance, cytotoxic side effects, cost, and adherence. Alternative treatment options are being investigated to overcome these challenges including discovery of new molecules with increased anti-viral activity and development of easily administrable drug formulations. In light of the difficulties associated with current HIV treatment measures, and in the continuing absence of a cure, the prevention of new infections has also arisen as a prominent goal among efforts to curtail the worldwide HIV pandemic. In this review, the authors summarize currently available anti-HIV drugs and their combinations for treatment, new molecules under clinical development and prevention methods, and discuss drug delivery formats as well as associated challenges and alternative approaches for the future.

show abstract

“…[5] Moreover, 1,4-DHPs are NAD(P)H mimetics and can be used in alkaloids synthesis. [6] Figure 1. Drugs belonging to the group of 1,4dihydropyridines that act as calcium channel blockers.…”

Section: Introductionmentioning

confidence: 99%

Organocatalytic Enantioselective Synthesis of 1,4‐Dihydropyridines

2017

Self Cite

View full text Add to dashboard Cite

This review aims to bring light upon a very interesting group of compounds, the 1,4-dihydropyridines (1,4-DHPs). These structures are well-known pharmacophores, used for many years to treat cardiovascular diseases because of their activity as calcium channel blockers. In addition, their potential as drugs to treat other affections has been recently exposed. The racemic synthesis of 1,4-DHPs has been well studied, while the asymmetric approaches are mainly based on the use of chiral auxiliaries or chiral resolutions. However, there are scarce examples regarding enantioselective organocatalytic methods. Herein, we will summarize the existing examples in this field of research. 1 Introduction 2 BINOL-derived phosphoric acid mediated organocatalysis 3 (Thio)urea mediated organocatalysis 4 Aminocatalysis 5 Dual catalysis 6 Summary and outlook

show abstract

Organocatalytic Transfer Hydrogenation and Hydrosilylation Reactions

Cited by 23 publications

References 226 publications

Rational Design of Simple Organocatalysts for the HSiCl3 Enantioselective Reduction of (E)-N-(1-Phenylethylidene)aniline

Rational Design of Simple Organocatalysts for the HSiCl3 Enantioselective Reduction of (E)-N-(1-Phenylethylidene)aniline

Pharmaceutical Approaches to HIV Treatment and Prevention

Organocatalytic Enantioselective Synthesis of 1,4‐Dihydropyridines

Contact Info

Product

Resources

About