Cooperative Use of VCD and XRD for the Determination of Tetrahydrobenzoisoquinolines Absolute Configuration: A Reliable Proof of Memory of Chirality and Retention of Configuration in Enediyne Rearrangements

Naubron, Jean-Valère; Campolo, Damien; Giorgi, Michel; Bertrand, M.; Nechab, Malek

doi:10.1002/chir.22221

Cited by 5 publications

(5 citation statements)

References 38 publications

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“…The determination of absolute configurations (AC) was mandatory to propose a mechanism. Different techniques enable AC determination; we have been interested by ECD and VCD 23…”

Section: Resultsmentioning

confidence: 99%

Organocopper‐Triggered Cyclisation of Conjugated Diene‐ynes: Diastereo‐ and Enantioselective Synthesis of Indenes

et al. 2015

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“…The determination of absolute configurations (AC) was mandatory to propose a mechanism. Different techniques enable AC determination; we have been interested by ECD and VCD 23…”

Section: Resultsmentioning

confidence: 99%

Organocopper‐Triggered Cyclisation of Conjugated Diene‐ynes: Diastereo‐ and Enantioselective Synthesis of Indenes

et al. 2015

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“…Azaheterocylic 41 and further derivatives with a quarternary stereocenter were obtained from the cascade rearrangement of chiral enediynes, which proceeded through radical intermediates. 77 More than One Stereogenic Center. VCD spectroscopy shows its full power when more than one stereocenter has to be determined simultaneously.…”

Section: Determinations Carried Out Using Vcd Spectroscopymentioning

confidence: 99%

“…The benzocyclobutenone 40 , for instance, is the product of an asymmetric α-aryllation of protected α-amino acids which proceeded via an intermediate enolate. Azaheterocylic 41 and further derivatives with a quarternary stereocenter were obtained from the cascade rearrangement of chiral enediynes, which proceeded through radical intermediates …”

Section: Demonstrating the Diversity Of Ac Determinations Carried Out...mentioning

confidence: 99%

Absolute Configurations of Synthetic Molecular Scaffolds from Vibrational CD Spectroscopy

2019

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Vibrational circular dichroism (VCD) spectroscopy is one of the most powerful techniques for the determination of absolute configurations (AC), as it does not require any specific UV/vis chromophores, no chemical derivatization, and no growth of suitable crystals. In the past decade, it has become increasingly recognized by chemists from various fields of synthetic chemistry such as total synthesis and drug discovery as well as from developers of asymmetric catalysts. This perspective article gives an overview about the most important experimental aspects of a VCD-based AC determination and explains the theoretical analysis. The comparison of experimental and computational spectra that leads to the final conclusion about the AC of the target molecules is described. In addition, the review summarizes unique VCD studies carried out in the period 2008−2018 that focus on the determination of unknown ACs of new compounds, which were obtained in its enantiopure form either through direct asymmetric synthesis or chiral chromatography.

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“…IR and VCD were calculated using DFT with the B3LYP and 6311+G (d,p) functional and basic set. Solvent effects (CH 2 Cl 2 ) were introduced using the polarizable continuum model IEF-PCM combined with SMD [58] quantum mechanical continuum solvation parameters [59].…”

Section: Alkaloidsmentioning

confidence: 99%

Vibrational Circular Dichroism: Recent Advances for the Assignment of the Absolute Configuration of Natural Products

Burgueño‐Tapia

Joseph‐Nathan

2015

Natural Product Communications

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Vibrational circular dichroism (VCD) emerged during the last decade as a reliable tool for the absolute configuration (AC) determination of organic compounds. The principles, instrumentation, and methodology applied prior to early 2013 were recently reviewed by us. Since VCD is a very dynamic field, the aim of this review is to update VCD advances for the AC assignment of terpenoids, aromatic compounds, alkaloids, and other natural products for the 2013-2014 period, when VCD was applied to the AC assignment of some 70 natural products. In addition, although discovered in 2012, a brief introduction to the VCD exciton coupling approach and its applications in natural products AC assignment is presented.

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Cooperative Use of VCD and XRD for the Determination of Tetrahydrobenzoisoquinolines Absolute Configuration: A Reliable Proof of Memory of Chirality and Retention of Configuration in Enediyne Rearrangements

Cited by 5 publications

References 38 publications

Organocopper‐Triggered Cyclisation of Conjugated Diene‐ynes: Diastereo‐ and Enantioselective Synthesis of Indenes

Organocopper‐Triggered Cyclisation of Conjugated Diene‐ynes: Diastereo‐ and Enantioselective Synthesis of Indenes

Absolute Configurations of Synthetic Molecular Scaffolds from Vibrational CD Spectroscopy

Vibrational Circular Dichroism: Recent Advances for the Assignment of the Absolute Configuration of Natural Products

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