Palladium catalyzed insertion of carbon monoxide into benzyl-tetrahydroisoquinolines

Pandey, Ganesh; Tiwari, K. P.

doi:10.1016/s0040-4020(01)92052-6

Cited by 26 publications

(13 citation statements)

References 17 publications

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“…R4, mehr als 20-30 YO C,C-Verkniipfung zu bewerkstelligen, und was noch vie1 schlimmer ist, oft nur mit einem der beiden Diastereoisomeren von L"). Auch die Pd-katalysierte Einschiebungvon CO unter HBr-Abspaltung(N-H + CO + BrAr-t N-CO-Ar + HBr), eine in anderen Fallen erf~lgreiche~~), auch auf die Cyclisierung zu nicht hydroxylierten Berberin-Alkaloiden anwendbare Methode [57], versagte: wir erhielten zwar mit dem Amino-bromester u-9b maximal 20 % des gewunschten Lactams, beobachteten aber praktisch keine Umsetztung mit den 'richtig' substituierten Derivaten u-oder 1-15b'"). 28) Wodurch der Vorteil unserer Methode, wahlweise das Ioder das u-Isomere zu liefern, hinfallig ware!…”

Section: )unclassified

“…s, CH-0); 4,14-3,88 (m, CH2N); 3,98 (s, CH30); 3,93 (s, CH30); 2,89-2,88 (m. ArCH,); 1,36 (s, t-Bu). ',C-NMR (20 MHz,CDC13): 177.57;152,87;147,Ol;145,44;140,71;129,14;122,39;119,57;118,50;117,28;108,49;106,76;100,82;83,74;62,29;58,05;56,88;42,43;39,15;29,13;28,18. MS: 454 ( < 1, MC' + I), 260 (90), 176 (39,1), 57 (100).…”

Section: U-[l-(2-brom-cc-hydrosy~-1234-tetrahydro-67-dimethoxyi~sunclassified

“…: C 53,78, H 4,98, N 2,57. 55; 146,23; 144,85; 139,75; 132.94; 129,23; 128,75; 127,32; 124.07; 109,06; 108,53; 100,42; 77,33; H-C(5)); 6.30 (s, H-C(8)); 6,16 (d, J = 5,2, CH-0); 5,97, 5,93 ( 2~, OCH2O); 4,65 (d, J = 5,2, CHN); 3,85 (s, MHz,CDCI,): 176,93;143,11;146,44;138,89;133,lO;129,34;129,13;128,79;127,25;126,28;123,91;112,57;11 1,89;78,07;58,34;56,OO;55,85;4033;38,71;29,27;27, (20 MHz,27,27;26,95;24,17;10,36. MS: 276 ( < I , Mf' + I), 174 (3,3), 132 (loo), 117 (4,7), 57 (8,…”

Section: 14 U-22-dimethylpropansaure-[a-(l234-tetrahydro-l-isounclassified

“…: C 77,96,H 7,86,N 4,26. CDCI,): 177,58;136,42;135,531;129,07;126,30;126,17;125,87;77.43;57,79;41,94;38,56;30,26;28.56;27,43; …”

Section: 14 U-22-dimethylpropansaure-[a-(l234-tetrahydro-l-isounclassified

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Diasteroselektive Hydroxyalkylierungen in 1‐Stellung von Tetrahydroisochinolinen und Synthese von Aporphin‐, Protoberberin‐ und Phthalid‐Alkaloider

Seebàch¹,

Isabelle²,

Max³

1987

Helvetica Chimica Acta

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Unsubstituted and 6,7-dialkoxy-N-pivaloyl-tetrahydroisoqu~nolines 1-3 are converted to l-bromomagnesium derivatives by sequential treatment with 1-BuLi (-75"/THF) and MgBrz.0Et2. Addition of the metalated tetrahydroisoquinolines to aliphatic or aromatic aldehydes occurs with relative topicity ul (Scheme 2). The I-hydroxyalkylated 2-pivaloyl-tetrahydroisoquinolines a of u-configuration thus obtained (14 examples) can be converted to free aminoalcohols c of either Ior u-configuration (9 examples; Scheme 3). The depivdloylation with retention (+ u-c) is best achieved by heating in EtOH/KOH, the conversion to 1 -aminoalcohols I-c by treatment with CF,COOH/(CF,CO),O (+ I -pivalates I-b), followed by alkaline saponification or by LiAIH4 reduction of the esters. The configuration of the products is assigned by 'H-NMR spectroscopy, by X-ray crystal structure analysis, by chemical correlation, and by comparison of the chemical properties of the Iand the u-isomers. The diastereoselective hydroxybenzylation of the tetrahydroisoquinoline is used for short syntheses of ushinsunine/ oliveroline (Scheme 4 ) , p-hydrastine, and ophiocarpine/epiophiocarpine (Scheme 6: aporphine, phthalide, and protoberberine alkaloids, respectively).

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Section: )unclassified

Section: U-[l-(2-brom-cc-hydrosy~-1234-tetrahydro-67-dimethoxyi~sunclassified

Section: 14 U-22-dimethylpropansaure-[a-(l234-tetrahydro-l-isounclassified

“…: C 77,96,H 7,86,N 4,26. CDCI,): 177,58;136,42;135,531;129,07;126,30;126,17;125,87;77.43;57,79;41,94;38,56;30,26;28.56;27,43; …”

Section: 14 U-22-dimethylpropansaure-[a-(l234-tetrahydro-l-isounclassified

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Diasteroselektive Hydroxyalkylierungen in 1‐Stellung von Tetrahydroisochinolinen und Synthese von Aporphin‐, Protoberberin‐ und Phthalid‐Alkaloider

Seebàch¹,

Isabelle²,

Max³

1987

Helvetica Chimica Acta

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“…1). [3][4][5][6][7][8][9][10][11][12] Until now, only racemic bharatamine 1 has been synthesized [13][14][15][16][17] with no synthesis of this protoberberine alkaloid in its optically active form being published. Among the different methods developed for the construction of a protoberberine skeleton, a growing interest in the lateral metallation methodology 18 has been observed over the last decade.…”

Section: Introductionmentioning

confidence: 99%

The asymmetric synthesis of (R)-(+)- and (S)-(−)-O-methylbharatamine

Chrzanowska

Dreas

2004

Tetrahedron: Asymmetry

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Some Synthetic Uses of Halides

Hoyle¹

2009

Patai's Chemistry of Functional Groups

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Introduction Functional Group Interconversion of Halides Carbon–Carbon Bond Formation Using Halides Preparation of Heterocyclic Compounds by C  Y Bond Formation Rearrangement of Halides Acknowledgements

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Palladium catalyzed insertion of carbon monoxide into benzyl-tetrahydroisoquinolines

Cited by 26 publications

References 17 publications

Diasteroselektive Hydroxyalkylierungen in 1‐Stellung von Tetrahydroisochinolinen und Synthese von Aporphin‐, Protoberberin‐ und Phthalid‐Alkaloider

Diasteroselektive Hydroxyalkylierungen in 1‐Stellung von Tetrahydroisochinolinen und Synthese von Aporphin‐, Protoberberin‐ und Phthalid‐Alkaloider

The asymmetric synthesis of (R)-(+)- and (S)-(−)-O-methylbharatamine

Some Synthetic Uses of Halides

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