Asymmetric synthesis of a chiral arsinophosphine via a metal template promoted asymmetric Diels–Alder reaction between diphenylvinylphosphine and 2-furyldiphenylarsine

Tan, Ken Seng; Liu, Fengli; Li, Yongxin; Tan, Geok‐Kheng; Leung, Pak‐Hing

doi:10.1016/j.jorganchem.2006.07.025

Cited by 14 publications

(8 citation statements)

References 31 publications

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“…Hence, after 7 days at rt, a mixture of 3 chelating diphosphines was obtained [128]. The same Pt precursor also allowed the formation of other optically pure cycloadducts, obtained after reaction between DPVP and 2-furyldiphenylarsine [129] or 2-diphenylphosphinofurane [130], or between PDVP and 2-diphenylphosphinofurane [131]. In the latter case, the control of the configuration of the chiral phosphorus atom is however lower than in the studies mentioned above since a 2:1 S P :R P ratio is obtained [131].…”

Section: Reactivity In Cycloaddition Reactionsmentioning

confidence: 95%

Alkenylphosphines: Applications in Synthesis, Catalysis and Coordination Chemistry

Julienne¹,

Toulgoat²,

Delacroix

et al. 2010

COC

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Alkenylphosphines are compounds of great interest in view of their structures. The most interesting feature is the carboncarbon double bond, which is directly linked to the phosphorus atom. Nucleophilic addition or cycloaddition reactions can take place at this unsaturation, which can also be used as a coordinating part in the presence of a metal. Thus, alkenylphosphines have found numerous applications in various fields of chemistry. They are useful intermediates in organic synthesis: numerous studies are devoted to their transformation into bidentate ligands, to their use as precursors for dendrimer and polymer chemistry or as ligand for homogeneous catalysis. Due to the presence of both the phosphorus atom and the carbon-carbon double bond, they are also of great interest in coordination chemistry and their different bonding modes have been largely documented. Moreover, after complexation to transition metal, a great amount of work has been carried out on their reactivity in cycloaddition reactions, as well as in functionalization of the carbon-carbon double bond and other miscellaneous reactions. These main applications will be reviewed hereafter.

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Section: Reactivity In Cycloaddition Reactionsmentioning

confidence: 95%

Alkenylphosphines: Applications in Synthesis, Catalysis and Coordination Chemistry

Julienne¹,

Toulgoat²,

Delacroix

et al. 2010

COC

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“…Biologically active compounds, such as pharmaceuticals, agrochemicals, fragrances, and flavors as well as functional materials, are indispensable in our daily life. 1 Many biological functions of these key molecules arise from specific molecular and chirality recognition. So preparation of optically active substances is a substantial challenging work for chemists in both academia and industry.…”

Section: Chiral Phosphinesmentioning

confidence: 99%

“…It is necessary to pile up of optically active building blocks, which must be with suitable configuration, functionality, and conformational rigidity or flexibility to generate the desired stereoselectivity in the target complex. 1 In meeting the demand, asymmetric synthesis has become to the most attractive approach that is on a par with other methods, including optical and enzymatic resolutions. 2 Enantiomerically pure phosphines have attracted great interest in transition metal catalyzed asymmetric reactions.…”

Section: Chiral Phosphinesmentioning

confidence: 99%

“…The other two dichloro complexes were recrystallized from CDCl 3 in the ratio of 4:1 as white prisms. The 31 P{ 1…”

Section: Preparation Of Dichloro Complexes For (S P )-139 and (S P )-140mentioning

confidence: 99%

“…The solvent was removed and the residue (brownish oil) was distilled (b.p. 120-122 o C, 0.6 mmHg) to give the product as a colourless viscous oil: 1.40 g (85% yield); the product was chromatographed on a silica column with dichloromethane-hexane as eluent yielding a colorless oil: 0.824 g (45% yield) 1. H NMR (CDCl 3 ): δ 6.40 (s, 2H, OC=CH), 7.28-7.46 (m, 7H, aromatics and Ph 2 PC=CH ), 7.52 (s, 2H, OCH).…”

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confidence: 99%

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Asymmetric synthesis of chiral phosphines and arsines promoted by organometallic complexes

Liu¹

Self Cite

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This thesis describes the development of chiral cyclometalated-amine templates promoted asymmetric reactions such as the Diels-Alder, hydrophosphination and hydroarsination reactions for the synthesis of chiral phosphine and chiral arsine ligands. The [4+2] Diels-Alder reactions involving 3-diphenylphosphinofuran and three phosphine functionalized dienophiles viz. diphenylvinylphosphine, diphenyl[(E)-2-(ethoxycarbonyl)vinyl]phosphine and divinylphenylphosphine were carried out by employing platinum complexes containing the ortho metalated (R)-(1-(dimethylamino)ethyl)naphthalene (R)-86 as the chiral template to generate the endo-cycladducts. In chapter 1 the cycloaddition reaction between diphenylvinylphosphine and di-(3-furyl)phenylphosphine is also presented. The chiral naphthylamine auxiliary in the isolated chelating diphosphine endo-cycloadduct metal template complexes could be removed chemoselectively by treatment with concentrated sulfuric acid, during which the oxanorbornene skeleton of the diphosphine metal complexes is inert to the acid treatment. Further ligand liberation from the resultant dichloro complexes using aqueous cyanide gave the free bis(diphenylphosphino)-substituted cycloadduct ligands which are air stable. The asymmetric [4+2] Diels-Alder reaction involving 3-diphenylphosphinofuran as the dienophile and 3,4-dimethyl-1-phenylphosphole, DMPP, as the cyclic diene was carried out by utilizing the platinum(II) template complex (R)-86 as the chiral

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C−As Bond Formation Reactions for the Preparation of Organoarsenic(III) Compounds

Tay

Pullarkat

2020

Chemistry An Asian Journal

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Potential widespread applications of organoarsenic chemistry have been limited by the inherent lack of safe and effective As−C bond formation reactions. Several alternative reagents and methods have been developed in the last few decades to address the hazards and drawbacks associated with traditional arsenic synthetic strategies. Herein, this minireview summarizes the advances made in nucleophilic, electrophilic, radical and metal‐mediated As(III)−C bond formations while specifically highlighting the behavior of arsenic synthons with various well‐established reagents (eg. Grignard reagents, organolithium compounds, organometallic reagents, radical initiators and Lewis/Brønsted bases). Avenues for asymmetric synthesis are also discussed, as are recent advances in organoarsenic chemistry suggesting that arsines exhibit novel reactivities independent from that of other relatively more well explored Group V cogeners.

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Asymmetric synthesis of a chiral arsinophosphine via a metal template promoted asymmetric Diels–Alder reaction between diphenylvinylphosphine and 2-furyldiphenylarsine

Cited by 14 publications

References 31 publications

Alkenylphosphines: Applications in Synthesis, Catalysis and Coordination Chemistry

Alkenylphosphines: Applications in Synthesis, Catalysis and Coordination Chemistry

Asymmetric synthesis of chiral phosphines and arsines promoted by organometallic complexes

C−As Bond Formation Reactions for the Preparation of Organoarsenic(III) Compounds

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