Helical Phosphorus Derivatives

Virieux, David; Sevrain, Nicolas; Ayad, Tahar; Pirat, Jean‐Luc

doi:10.1016/bs.aihch.2015.06.001

Cited by 10 publications

(5 citation statements)

References 77 publications

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“…Since various helicene-based phosphine-related ligands have been reviewed [2,5,[7][8][9], only recent selected examples capable of delivering exceptionally high ee values are summarized here.…”

Section: Helicenes As Chiral Catalystsmentioning

confidence: 99%

“…Thus, chromatographically separated endo-76 effectively catalyzes the enantioselective cycloisomerization of N-tethered 1,6-enyne 78 to give bicyclo[4.1.0]heptane 79 with 95% yield and 81% ee, whilst exo-77 remained almost inactive [56] (Scheme 12). Meanwhile, various phosphole-containing ligands were also prepared and screened in similar reactions with success [8,9,57]. Scheme 11.…”

Section: Scheme 11mentioning

confidence: 99%

“…In 2016, Sako et al successfully used the modified BINOL-based vanadium(V) complex 204, capable of functioning both as redox and Lewis acid catalysts, for the enantioselective synthesis of oxa [9]helicenes 205 starting from polycyclic phenols 206. The reaction proceeds via oxidative coupling at first, followed by intramolecular cyclization.…”

Section: Enantiopure Helicenes: Enantioselective Synthesis Chiral Sementioning

confidence: 99%

“…The reaction proceeds via oxidative coupling at first, followed by intramolecular cyclization. This results in the one-step enantioselective synthesis of oxa [9]helicenes in good yields with up to 94% ee [111] (Scheme 36). Besides the optical resolution of racemates, another approach to enantiopure helicenes is based on the stereospecific synthesis, where the originally chiral precursors or reagents are converted into the corresponding helicenes with unidirectional helicity [110].…”

Section: Enantiopure Helicenes: Enantioselective Synthesis Chiral Sementioning

confidence: 99%

“…The reaction proceeds via oxidative coupling at first, followed by intramolecular cyclization. This results in the one-step enantioselective synthesis of oxa [9]helicenes in good yields with up to 94% ee [111] (Scheme 36). In 2015, a new general asymmetric synthetic methodology was successfully developed for [5]-, [6]-, and [7]helicenes with ultimate enantioselectivity (ee >99) based on the controlled transfer of reactant point chirality to the product with unidirectional helicity [112].…”

Section: Enantiopure Helicenes: Enantioselective Synthesis Chiral Sementioning

confidence: 99%

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Helicene-Based Chiral Auxiliaries and Chirogenesis

Hasan

Borovkov

2017

Symmetry

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Helicenes are unique helical chromophores possessing advanced and well-controlled spectral and chemical properties owing to their diverse functionalization and defined structures. Specific modification of these molecules by introducing aromatic rings of differing nature and different functional groups results in special chiroptical properties, making them effective chiral auxiliaries and supramolecular chirogenic hosts. This review aims to highlight these distinct structural features of helicenes; the different synthetic and supramolecular approaches responsible for their efficient chirality control; and their employment in the chirogenic systems, which are still not fully explored. It further covers the limitation, scope, and future prospects of helicene chromophores in chiral chemistry.

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Section: Helicenes As Chiral Catalystsmentioning

confidence: 99%

Section: Scheme 11mentioning

confidence: 99%

Section: Enantiopure Helicenes: Enantioselective Synthesis Chiral Sementioning

confidence: 99%

Section: Enantiopure Helicenes: Enantioselective Synthesis Chiral Sementioning

confidence: 99%

“…The reaction proceeds via oxidative coupling at first, followed by intramolecular cyclization. This results in the one-step enantioselective synthesis of oxa [9]helicenes in good yields with up to 94% ee [111] (Scheme 36). In 2015, a new general asymmetric synthetic methodology was successfully developed for [5]-, [6]-, and [7]helicenes with ultimate enantioselectivity (ee >99) based on the controlled transfer of reactant point chirality to the product with unidirectional helicity [112].…”

Section: Enantiopure Helicenes: Enantioselective Synthesis Chiral Sementioning

confidence: 99%

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Helicene-Based Chiral Auxiliaries and Chirogenesis

Hasan

Borovkov

2017

Symmetry

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ChemInform Abstract: Helical Phosphorus Derivatives: Synthesis and Applications

et al. 2016

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A Palladium‐Catalyzed Decarboxylative Heck‐Type Reaction of Disubstituted Vinylphosphonates in the Stereoselective Synthesis of Trisubstituted Vinylphosphonates

Ren

Ran

et al. 2019

Eur J Org Chem

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We describe a highly stereoselective and atomically economical approach for the preparation of trisubstituted vinylphosphonates through palladium‐catalyzed decarboxylative Heck‐type reactions of vinylphosphonates. Excellent E/Z selectivity was achieved mostly with E‐isomers; this was difficult to achieve via traditional methods. Oxygen in the air was the sole oxidant, and this minimizes the use of high‐loading silver or other species. This work is the first example to synthesize vinylphosphonates via a catalyzed decarboxylative Heck‐type reaction.

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Helical Phosphorus Derivatives

Cited by 10 publications

References 77 publications

Helicene-Based Chiral Auxiliaries and Chirogenesis

Helicene-Based Chiral Auxiliaries and Chirogenesis

ChemInform Abstract: Helical Phosphorus Derivatives: Synthesis and Applications

A Palladium‐Catalyzed Decarboxylative Heck‐Type Reaction of Disubstituted Vinylphosphonates in the Stereoselective Synthesis of Trisubstituted Vinylphosphonates

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