Stereoselektive arenbildende Aldolkondensation: Synthese konfigurativ stabiler Oligo‐1,2‐naphthylene

Lotter, Dominik; Neuburger, Markus; Rickhaus, Michel; Häußinger, Daniel; Sparr, Christof

doi:10.1002/ange.201510259

Cited by 45 publications

(4 citation statements)

References 40 publications

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“…Sparr et al. reported an exceptionally high rotational barrier of Δ G ≠ 453 K =36.8 kcal mol −1 for tri‐ ortho ‐substituted oligo‐1,2‐naphthylenes and concluded that the rotation of their aryl‐aryl bonds was sufficiently restricted to form discrete stereoisomers [3c] . Therefore, the conformers of quaternaphthalene 6 are also considered to exist as discrete stereoisomers, which is in contrast to those of quaterazulene 2 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Properties of Twisted and Helical Azulene Oligomers and Azulene‐Based Polycyclic Hydrocarbons

Tsuchiya,

Higashibeppu,

Mazaki

2023

ChemistryOpen

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The construction of 1,2‐position‐connected azulene oligomers was achieved. In the crystal packing structure of the terazulene, two molecules of (Ra)‐ and (Sa)‐configurations formed a pair. Variable temperature NMR measurements and theoretical calculations of the quaterazulene suggest that the helical and syn‐type structure with terminal azulene overlap is more stable. Two kinds of fused terazulenes (1,2′′‐closed and 1,8′′‐closed) were also synthesized by intramolecular Pd‐catalyzed C−H/C−Br arylation of the terazulene moieties. X‐ray structure analysis of 1,2′′‐closed terazulene revealed a planar structure, while an analysis of 1,8′′‐closed terazulene performed on a C60 co‐crystal revealed a curved structure forming a 1 : 1 complex covering the co‐crystal. Nucleus‐independent chemical shift (NICS) calculations carried out for the central seven‐membered ring of 1,8′′‐closed terazulene showed a positive value, suggesting anti‐aromatic properties.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Properties of Twisted and Helical Azulene Oligomers and Azulene‐Based Polycyclic Hydrocarbons

Tsuchiya,

Higashibeppu,

Mazaki

2023

ChemistryOpen

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“…Based on this reactivity, Sparr group developed a strategy for the efficient synthesis of oligo‐1,2‐naphthylenes in 2016 (Scheme ) . Double oxidation of 20 led to a ketoaldehyde intermediate, followed by stereoselective arene‐forming via aldol condensation by using chiral amino‐acid 21 as the catalyst to generate ternaphthalene 22 with excellent enantioselective control.…”

Section: Atropselective Synthesis Of Biarylsmentioning

confidence: 99%

Construction of Axially Chiral Compounds via Central‐to‐Axial Chirality Conversion

Hui

Chen

Zhou

2020

Chemistry An Asian Journal

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Central-to-axial chirality conversion represents a fascinating class of chemical processes consisting of the destruction of stereogenic centers and the simultaneous installation of axial chiral elements, which provides efficient methods for the preparation of axially chiral compounds. Using the strategy, a wide range of axially chiral compounds, including biaryls, heterobiaryls, aromatic amides, allenes and vinyl arenes, have been synthesized with high efficiency and excellent enantioselectivity. In addition, central-to-axial chirality conversion strategy has been applied to the synthesis of natural products. The strategy has undoubtedly become and will continue to be a hot research topic in the field of asymmetric catalysis and synthesis. In this minireview, we selected some examples to introduce the developments and trends in the central-to-axial chirality conversion strategy up to April 2020.

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“…A third ortho ‐substituent that is contained in the oligo‐1,2‐naphthylene structure consequently hinders rotation in both directions. Due to the resulting high rotational barriers, a pronounced configurational stability for each stereogenic axis was expected (Figure c) …”

Section: Oligo‐12‐naphthylenesmentioning

confidence: 99%

Stereoselective Arene‐Forming Aldol Condensation: Catalyst‐Controlled Synthesis of Axially Chiral Compounds

Witzig

Lotter

Fäseke

et al. 2017

Chemistry A European J

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The fundamental role that aldol chemistry adopts in various disciplines, such as stereoselective catalysis or the biosynthesis of aromatic polyketides, illustrates its exceptional versatility. On the one hand, numerous aldol addition reactions reliably transfer the stereochemical information from catalysts into various valuable products. On the other hand, countless aromatic polyketide natural products are produced by an ingenious biosynthetic machinery based on arene-forming aldol condensations. With the aim of complementing aldol methodology that controls stereocenter configuration, we recently combined these two tenets by investigating small-molecule-catalyzed aldol condensation reactions that stereoselectively form diverse axially chiral compounds through the construction of a new aromatic ring.

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Stereoselektive arenbildende Aldolkondensation: Synthese konfigurativ stabiler Oligo‐1,2‐naphthylene

Cited by 45 publications

References 40 publications

Synthesis and Properties of Twisted and Helical Azulene Oligomers and Azulene‐Based Polycyclic Hydrocarbons

Synthesis and Properties of Twisted and Helical Azulene Oligomers and Azulene‐Based Polycyclic Hydrocarbons

Construction of Axially Chiral Compounds via Central‐to‐Axial Chirality Conversion

Stereoselective Arene‐Forming Aldol Condensation: Catalyst‐Controlled Synthesis of Axially Chiral Compounds

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