Synthesis of optically active cyclopalladated complexes of primary benzylamine derivatives, (R)-(−)-2-phenylglycine methyl ester and (±)-1-phenylethylamine

Fuchita, Yoshio; Yoshinaga, Keiji; Ikeda, Yuki; Kinoshita-Kawashima, Junko

doi:10.1039/a608622e

Cited by 57 publications

(44 citation statements)

References 30 publications

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“…It should be noted that complete racemization of both Schiff bases takes place during the cyclopalladation reaction, but by contrast, racemization does not occur during the cyclopalladation of the 2-phenylglycine methyl ester. [6] This fact can be related to the increased acidity of the H a atom in these metallacycles (see below).…”

Section: Resultsmentioning

confidence: 96%

Deamination of the Amino Acid Fragment in Imine Metallacycles: Unexpected Synthesis of an NH‐Aldimine Organometallic Compound

Albert

Cadena

González

et al. 2006

Chemistry A European J

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We report that the action of Lewis bases, such as triphenylphosphine, pyridine, or trimethylamine, on imine metallacycles derived from amino acids leads to the formation of the first organometallic compound of an NH aldimine, a highly reactive organic species, and the corresponding alpha-ketoester, in a deamination reaction that mimics the metabolism of alpha-amino acids. The synthesis of different cyclopalladated compounds by a reaction between palladium acetate and the Schiff bases 2,4,6-Me(3)C(6)H(2)CH=NCH(R(1))COOR(2) (R(1) = CH(2)Ph, R(2) = Et and R(1) = Ph, R(2) = Me) is also reported.

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Section: Resultsmentioning

confidence: 96%

Deamination of the Amino Acid Fragment in Imine Metallacycles: Unexpected Synthesis of an NH‐Aldimine Organometallic Compound

Albert

Cadena

González

et al. 2006

Chemistry A European J

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“…The palladium-organic cations were obtained according to Scheme 1. The primary amines 1-phenylethylamine and 1-(4-methylphenyl)ethylamine were cyclopalladated and converted to chloro-bridged dinuclear complexes by well-established methods [16,17]. Related dinuclear compounds, mostly naphtyl rather than phenyl derivatives, have been used successfully for resolution via formation of diastereomers [18][19][20][21].…”

Section: Resultsmentioning

confidence: 99%

Unexpected solids from enantiopure cationic palladium complexes and racemic anions: A structural study of chiral non-discrimination

Kalf

Wang

Englert

2006

Journal of Organometallic Chemistry

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“…Several reports have been published by Fuchita et al [22,23], Vicente et al [24], Albert et al [25] and our laboratory [26] that infringe the Cope's rules. For the first time, Vicente et al [27] reported the synthesis of six-membered palladacycles from primary amines with electron-withdrawing substituents that break down all conditions of Cope's rules.…”

Section: Introductionmentioning

confidence: 89%

Synthesis and characterization of 2-phenylaniline cyclopalladated complexes

Karami

Rizzoli

Rahimi

2011

Transition Met Chem

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Reaction of the dinuclear complex [Pd{j2-N2 0 ,C1-2-(2 0 -NH 2 C 6 H 4 )C 6 H 4 }Cl] 2 (1) with ligands (L = 4-picoline, sym-collidine) gave the six-membered palladacycles [Pd{j2-N2 0 ,C1-2-(2 0 -NH 2 C 6 H 4 )C 6 H 4 }Cl(L)] (2). The complex 1 reacted with AgX (X = CF 3 SO 3 , BF 4 ) and bidentate ligands [L-L = phen (phenanthroline), dppe (bis(diphenylphosphino)ethane), bipy(2,2 0 -bipyridine) and dppp (bis(diphenylphosphino)propane)] giving the mononuclear orthopalladated complexes [Pd{j2-N2 0 ,C1-2-(2 0 -NH 2 C 6 H 4 )C 6 H 4 }(L-L)] (3) [L-L = phen, dppe, bipy and dppp]. These compounds were characterized by physicochemical methods, and the structure of [Pd{j2-N2 0 ,C1-2-(2 0 -NH 2 C 6 H 4 )C 6 H 4 }Cl(L)] (L = sym-collidine) was determined by single-crystal X-ray analysis.

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Synthesis of optically active cyclopalladated complexes of primary benzylamine derivatives, (R)-(−)-2-phenylglycine methyl ester and (±)-1-phenylethylamine

Cited by 57 publications

References 30 publications

Deamination of the Amino Acid Fragment in Imine Metallacycles: Unexpected Synthesis of an NH‐Aldimine Organometallic Compound

Deamination of the Amino Acid Fragment in Imine Metallacycles: Unexpected Synthesis of an NH‐Aldimine Organometallic Compound

Unexpected solids from enantiopure cationic palladium complexes and racemic anions: A structural study of chiral non-discrimination

Synthesis and characterization of 2-phenylaniline cyclopalladated complexes

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