Samarium Iodobinaphtholate: An Efficient Catalyst for Enantioselective Aza‐Michael Additions of <i>O</i>‐Benzylhydroxylamine to <i>N</i>‐Alkenoyloxazolidinones

Didier, Dorian; Meddour, Abdelkrim; Bezzenine‐Lafollée, Sophie; Collin, Jacqueline

doi:10.1002/ejoc.201100041

Cited by 23 publications

(7 citation statements)

References 60 publications

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“…Most recently, asymmetric hydroxyamination of α,β-unsaturated imidazoles catalyzed by the chiral-at-metal complex L31−Rh(III) was reported by Kang et al 408 A series of N-protected hydroxyl amines and α,βunsaturated imidazoles were tolerated, providing the corresponding adducts in both high yields and ee's (up to 91% yield and 99% ee; Scheme 99c). Collin and co-workers 409,410 successfully developed a simple samarium-iodobinaphtholatepromoted addition of aromatic amines and O-benzylhydroxylamine to α,β-unsaturated N-alkenoyloxazolidinones (up to 88% ee). useful in the fields of asymmetric catalysis, pharmaceutical chemistry, and materials.…”

Section: Conjugate Addition Of Nitrogen Nucleophilesmentioning

confidence: 99%

Recent Advances in Metal-Catalyzed Asymmetric 1,4-Conjugate Addition (ACA) of Nonorganometallic Nucleophiles

2018

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The metal-catalyzed asymmetric conjugate addition (ACA) reaction has emerged as a general and powerful approach for the construction of optically active compounds and is among the most significant and useful reactions in synthetic organic chemistry. In recent years, great progress has been made in this area with the use of various chiral metal complexes based on different chiral ligands. This review provides comprehensive and critical information on the enantioselective 1,4-conjugate addition of nonorganometallic (soft) nucleophiles and their importance in synthetic applications. The literature is covered from the last 10 years, and a number of examples from before 2007 are included as background information. The review is divided into multiple parts according to the type of nucleophile involved in the reaction (such as C-, B-, O-, N-, S-, P-, and Si-centered nucleophiles) and metal catalyst systems used.

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Section: Conjugate Addition Of Nitrogen Nucleophilesmentioning

confidence: 99%

Recent Advances in Metal-Catalyzed Asymmetric 1,4-Conjugate Addition (ACA) of Nonorganometallic Nucleophiles

2018

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“…Collin and co-workers also expanded this methodology to the 1,4-addition of O -benzylhydroxylamine [ 245 ] ( Scheme 37 ). Like the previous reactions, the formation of the undesired side product could be reduced by lowering the reaction temperature to −40 °C.…”

Section: Reviewmentioning

confidence: 99%

Diastereoselective and enantioselective conjugate addition reactions utilizing α,β-unsaturated amides and lactams

Byrd¹

2015

Beilstein J. Org. Chem.

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SummaryThe conjugate addition reaction has been a useful tool in the formation of carbon–carbon bonds. The utility of this reaction has been demonstrated in the synthesis of many natural products, materials, and pharmacological agents. In the last three decades, there has been a significant increase in the development of asymmetric variants of this reaction. Unfortunately, conjugate addition reactions using α,β-unsaturated amides and lactams remain underdeveloped due to their inherently low reactivity. This review highlights the work that has been done on both diastereoselective and enantioselective conjugate addition reactions utilizing α,β-unsaturated amides and lactams.

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“…In agreement with the initial analytical aim, 13 C-{ 1 H} 1D NMR in CLCs was rapidly applied to investigate the enantioselectivity of various asymmetric syntheses. Such cases included the double diastereoselection in [2+3] cycloaddition reactions of chiral oxazoline n-oxides and their application to the kinetic resolution of a racemic α,β-unsaturated δ-lactone [213], the intramolecular hydroamination catalysed by neutral rare-earth catalytic or ate complexes [214,215], or the aza-Michael additions of Obenzylhydroxylamine to N-alkenoyloxazolidinones catalysed by samarium iodobinaphtholate [216].…”

Section: Examples Of Applications In Asymmetric Synthesismentioning

confidence: 99%

Multinuclear NMR in polypeptide liquid crystals: Three fertile decades of methodological developments and analytical challenges

Lesot

Aroulanda

Berdagué

et al. 2020

Progress in Nuclear Magnetic Resonance Spectroscopy

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NMR spectroscopy of oriented samples makes accessible residual anisotropic intramolecular NMR interactions, such as chemical shift anisotropy (RCSA), dipolar coupling (RDC), and quadrupolar coupling (RQC), while preserving high spectral resolution. In addition, in a chiral aligned environment, enantiomers of chiral molecules or enantiopic elements of prochiral compounds adopt different average orientations on the NMR timescale, and hence produce distinct NMR spectra or signals. NMR spectroscopy in chiral aligned media is a powerful analytical tool, and notably provides unique information on (pro)chirality analysis, natural isotopic fractionation, stereochemistry, as well as molecular conformation and configuration. Significant progress has been made in this area over the three last decades, particularly using polypeptide-based chiral liquid crystals (CLCs) made of organic solutions of helically chiral polymers (as PBLG) in organic solvents. This review presents an overview of NMR in polymeric LCs. In particular, we describe the theoretical tools and the major NMR methods that have been developed and applied to study (pro)chiral molecules dissolved in such oriented solvents. We also discuss the representative applications illustrating the analytical potential of this original NMR tool. This overview article is dedicated to thirty years of original contributions to the development of NMR spectroscopy in polypeptide-based chiral liquid crystals.

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Samarium Iodobinaphtholate: An Efficient Catalyst for Enantioselective Aza‐Michael Additions of O‐Benzylhydroxylamine to N‐Alkenoyloxazolidinones

Cited by 23 publications

References 60 publications

Recent Advances in Metal-Catalyzed Asymmetric 1,4-Conjugate Addition (ACA) of Nonorganometallic Nucleophiles

Recent Advances in Metal-Catalyzed Asymmetric 1,4-Conjugate Addition (ACA) of Nonorganometallic Nucleophiles

Diastereoselective and enantioselective conjugate addition reactions utilizing α,β-unsaturated amides and lactams

Multinuclear NMR in polypeptide liquid crystals: Three fertile decades of methodological developments and analytical challenges

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