Asymmetric induction in an enammonium-iminium rearrangement. Mechanistic insight via NMR, deuterium labeling, and reaction rate studies. Application to the stereoselective synthesis of pyrroloisoquinoline antidepressants

Sorgi, Kirk L.; Maryanoff, Cynthia A.; McComsey, David F.; Graden, David W.; Maryanoff, Bruce E.

doi:10.1021/ja00165a048

Cited by 68 publications

(26 citation statements)

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“…[18][19][20] In spite of these efforts, there are few general methods for the asymmetric synthesis of these compounds. [21][22][23][24] Lee et al reported the total synthesis of both enantiomers of parent 16. 25,26) The overall yields of their synthesis are 10.0% for the R isomer (6 steps from L-tartaric acid and 2-phenethylamine), and 6.1% for the S isomer (8 steps from malic acid and 2-phenethylamine), respectively.…”

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confidence: 99%

The Synthesis of Isoquinoline Alkaloid and Its Related Compounds Using Alanine Derivatives as Chiral Auxiliaries

et al. 2003

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Chiral 1-substituted isoquinoline derivatives, which were obtained by the reaction using alanine derivatives as chiral auxiliaries, were transformed to (S)-2,3,9,10,11-pentamethoxyhomoprotoberberine (7) and a synthetic intermediate for O-methylkreysigine (9) in good yields and high stereoselectivity. The corresponding chiral allyl derivative of isoquinoline was transformed to a pyrrolidinoisoquinoline (16) in a highly enantioselective manner.

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confidence: 99%

The Synthesis of Isoquinoline Alkaloid and Its Related Compounds Using Alanine Derivatives as Chiral Auxiliaries

et al. 2003

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“…[194,195] In some cases the intermediate â-oxo lactam 41 is isolated because of partial polymerization of the oxo lactam intermediate under the strong acidic conditions required for N-dealkylation. [196,197] This procedure also allows the preparation of 4,5-disubstituted 3,4-dihydro-2H-pyrroles 44 via an extra alkylation step of the oxo lactam 41 with an alkyl halide. By refluxing the resulting oxo lactam 43 with 6 M hydrochloric acid, the disubstituted derivatives 44 are obtained in moderate to excellent yield (Scheme 19).…”

Section: Variation 3: By Hydrolysis Of N-vinyl Lactamsmentioning

confidence: 99%

“…This methodology also has been expanded using functionalized esters such as ethyl 3-(3-bromo-4-pyridyl)propanoate [198] and ethyl 5-bromonicotinate. [199] Scheme 19 Synthesis of 5-Monosubstituted and 4,5-Disubstituted 3,4-Dihydro-2H-pyrroles [194,196,197 5-Isopropyl-3,4-dihydro-2H-pyrrole (42, R 1 = iPr); Typical Procedure: [197] A mixture of freshly distilled 1-vinyl-2-pyrrolidone (40; 8.3 g, 75 mmol) and methyl 2methylpropanoate (9.2 g, 90 mmol) in THF (20 mL) was slowly added to 95% NaH (4.8 g, 190 mmol) in refluxing THF (80 mL). The mixture was refluxed for 4 h, cooled to rt, diluted with sat.…”

Section: Variation 3: By Hydrolysis Of N-vinyl Lactamsmentioning

confidence: 99%

Product Class 7: Imines

Padwa¹,

Bellus²

2005

Category 4. Compounds With Two Carbon Heteroatom Bonds

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Compounds with the general structure R 1 R 2 C=NR 3 , referred to as imines, were first obtained by Schiff via condensation of ketones and aldehydes with primary amines. Therefore, the condensation products are also called Schiff bases. In addition, the nominations azomethine, ketimine (derived from ketones), aldimine (derived from aldehydes), and anil (derived from anilines) are in use. It is recommended that the terms imine(s), ketimine(s), or aldimine(s) are used, rather than Schiff base(s) or azomethine(s).Since imines have to be considered as analogues of carbonyl compounds, many of the chemical properties are similar to the latter. Imines are used in new C-C bond formations, and reactions with electrophiles (e.g., aldehydes, alkyl halides), and the C=N moiety can undergo nucleophilic reactions. Generally, imines are very useful compounds in organic synthesis, as they are used in several syntheses of aza-heterocyclic compounds. Most imines are stable in an alkaline medium and therefore can be dried over potassium hydroxide. In diluted acid, however, they are easily hydrolyzed. In many cases intermediary imines cannot be isolated because of their lability. The presence of a C=N bond creates the possibility for E/Z isomerism (syn/anti). It has been recognized that such geomet-

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“…Synthesis of pyrrolo[2,1-a]isoquinoline moieties have received much attention as they possess various biological activity 9,10 and serve as intermediates for the synthesis of bioactive alkaloids [11]. Moreover, this type of compounds can be used as Positron Emission Tomography(PET) radiotracers for imaging serotonin uptake sites [12].The varied biological activities of pyrrolo [2,1-a]isoquinoline derivatives have attracted the attention of organic chemists and a number of synthetic methodologies have been developed for this system [13][14][15][16][17][18][19][20].…”

Section: …………………………………………………………………………………………………… Introduction:-mentioning

confidence: 99%

SOLVENT FREE SYNTHESIS OF PYRROLO[2,1-a]ISOQUINOLINES UNDER MICROWAVE-IRRADIATION: AN ANTIOXIDANT POTENT.

Mukherjee¹

2018

IJAR

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Asymmetric induction in an enammonium-iminium rearrangement. Mechanistic insight via NMR, deuterium labeling, and reaction rate studies. Application to the stereoselective synthesis of pyrroloisoquinoline antidepressants

Cited by 68 publications

References 0 publications

The Synthesis of Isoquinoline Alkaloid and Its Related Compounds Using Alanine Derivatives as Chiral Auxiliaries

The Synthesis of Isoquinoline Alkaloid and Its Related Compounds Using Alanine Derivatives as Chiral Auxiliaries

Product Class 7: Imines

SOLVENT FREE SYNTHESIS OF PYRROLO[2,1-a]ISOQUINOLINES UNDER MICROWAVE-IRRADIATION: AN ANTIOXIDANT POTENT.

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