Rhodium(II)‐Catalyzed Enantioselective Synthesis of Troponoids

Murarka, Sandip; Jia, Zhijun; Merten, Christian; Daniliuc, Constantin G.; Antonchick, Andrey P.; Waldmann, Herbert

doi:10.1002/ange.201502233

Cited by 4 publications

(1 citation statement)

References 66 publications

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“…67 Further examples are propellane 34 (which may be considered axially chiral as well), 68 the building block for α v β 6 integrin inhibitors 35, 69 the products of the anodic oxidation of 2,4-dimethylphenol such as 36, 70 the bioactive spiropyrazolone derivatives 37, 71 and the lactone 38. 72 Stoltz and co-workers investigated the enantioselective Pd-catalyzed allylic alkylation yielding dialkylated N-heterocycles such as 74 are interesting examples from a field of asymmetric synthesis, which takes advantage of the concept of memory of chirality (MOC). 75 A particular characteristic of such MOC reactions is that they take place via chiral enolate or radical species with rather short half-life times of racemization which leads to a competition between the actual reaction of the chiral intermediate with its racemization.…”

Section: Determinations Carried Out Using Vcd Spectroscopymentioning

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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Section: Determinations Carried Out Using Vcd Spectroscopymentioning

confidence: 99%

Absolute Configurations of Synthetic Molecular Scaffolds from Vibrational CD Spectroscopy

2019

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The Synthesis, Structural Characterisation and Chemical Manipulation of the [6+3] Cycloadduct Derived from α‐Tropolone O‐Methyl Ether and Trimethylenemethane

et al. 2019

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The title bicyclic system 3, the adduct arising from the formal [6 + 3] cycloaddition of α-tropolone O-methyl ether (1) and trimethylenemethane (2), has been prepared and subject to single-crystal X-ray analysis. The chemical manipulation of adduct 3 in a range of ways is reported, including through acid-catalysed rearrangement of the derived mono-oxide to give the bicyclo[4.3.1]undecane 21. Scheme 1. The previously reported [3] [6 + 3] cycloaddition of troponoid 1 with TMM (2) leading to adduct 3.

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Asymmetric Total Synthesis of (−)‐Englerin A through Catalytic Diastereo‐ and Enantioselective Carbonyl Ylide Cycloaddition

Hanari

Shimada

Kurosaki

et al. 2015

Chemistry A European J

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An asymmetric total synthesis of the guaiane sesquiterpene (−)‐englerin A, a potent and selective inhibitor of the growth of renal cancer cell lines, was accomplished. The basis of the approach is a highly diastereo‐ and enantioselective carbonyl ylide cycloaddition with an ethyl vinyl ether dipolarophile under catalysis by dirhodium(II) tetrakis[N‐tetrachlorophthaloyl‐(S)‐tert‐leucinate], [Rh2(S‐TCPTTL)4], to construct the oxabicyclo[3.2.1]octane framework with concomitant introduction of the oxygen substituent at C9 on the exo‐face. Another notable feature of the synthesis is ruthenium tetraoxide‐catalyzed chemoselective oxidative conversion of C9 ethyl ether to C9 acetate.

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Rhodium(II)‐Catalyzed Enantioselective Synthesis of Troponoids

Cited by 4 publications

References 66 publications

Absolute Configurations of Synthetic Molecular Scaffolds from Vibrational CD Spectroscopy

Absolute Configurations of Synthetic Molecular Scaffolds from Vibrational CD Spectroscopy

The Synthesis, Structural Characterisation and Chemical Manipulation of the [6+3] Cycloadduct Derived from α‐Tropolone O‐Methyl Ether and Trimethylenemethane

Asymmetric Total Synthesis of (−)‐Englerin A through Catalytic Diastereo‐ and Enantioselective Carbonyl Ylide Cycloaddition

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