Diastereomerically pure pyrrolidin-2-ones by intramolecular Michael reaction. Synthesis of both (S)- and (R)-3-pyrrolidineacetic acid

Roberta Galeazzi; Silvano Geremia; Giovanna Mobbili; Mario Orena

doi:10.1016/0957-4166(95)00423-8

Diastereomerically pure pyrrolidin-2-ones by intramolecular Michael reaction. Synthesis of both (S)- and (R)-3-pyrrolidineacetic acid

Roberta Galeazzi, Silvano Geremia, Giovanna Mobbili, Mario Orena

Istituto Nazionale di Riposo e Cura per Anziani V.E. II

Research output: Contribution to journal › Article › peer-review

Abstract

By intramolecular conjugate addition of their derived enolates, the amides 5 and 6 gave diastereomeric mixtures of pyrrolidin-2-ones 10,11 and 12,13, in good yield and 80:20 d.r. After chromatographic separation, the configuration of pure diastereomers was assigned from ¹H NMR data. The usefulness of this intramolecular cyclisation was proven by conversion of either 10 or 12 into pyrrolidin-2-one 14 which through simple steps gave (S)-3-pyrrolidineacetic acid, 2. Following the same synthetic scheme, but starting from either 11 or 13, (R)-3-pyrrolidineacetic acid 3 was obtained.

Original language	English
Pages (from-to)	79-88
Number of pages	10
Journal	Tetrahedron: Asymmetry
Volume	7
Issue number	1
DOIs	https://doi.org/10.1016/0957-4166(95)00423-8
Publication status	Published - 1996

ASJC Scopus subject areas

Inorganic Chemistry
Organic Chemistry
Materials Chemistry
Drug Discovery

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abstract = "By intramolecular conjugate addition of their derived enolates, the amides 5 and 6 gave diastereomeric mixtures of pyrrolidin-2-ones 10,11 and 12,13, in good yield and 80:20 d.r. After chromatographic separation, the configuration of pure diastereomers was assigned from 1H NMR data. The usefulness of this intramolecular cyclisation was proven by conversion of either 10 or 12 into pyrrolidin-2-one 14 which through simple steps gave (S)-3-pyrrolidineacetic acid, 2. Following the same synthetic scheme, but starting from either 11 or 13, (R)-3-pyrrolidineacetic acid 3 was obtained.",

author = "Roberta Galeazzi and Silvano Geremia and Giovanna Mobbili and Mario Orena",

year = "1996",

doi = "10.1016/0957-4166(95)00423-8",

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T1 - Diastereomerically pure pyrrolidin-2-ones by intramolecular Michael reaction. Synthesis of both (S)- and (R)-3-pyrrolidineacetic acid

AU - Galeazzi, Roberta

AU - Geremia, Silvano

AU - Mobbili, Giovanna

AU - Orena, Mario

PY - 1996

Y1 - 1996

N2 - By intramolecular conjugate addition of their derived enolates, the amides 5 and 6 gave diastereomeric mixtures of pyrrolidin-2-ones 10,11 and 12,13, in good yield and 80:20 d.r. After chromatographic separation, the configuration of pure diastereomers was assigned from 1H NMR data. The usefulness of this intramolecular cyclisation was proven by conversion of either 10 or 12 into pyrrolidin-2-one 14 which through simple steps gave (S)-3-pyrrolidineacetic acid, 2. Following the same synthetic scheme, but starting from either 11 or 13, (R)-3-pyrrolidineacetic acid 3 was obtained.

AB - By intramolecular conjugate addition of their derived enolates, the amides 5 and 6 gave diastereomeric mixtures of pyrrolidin-2-ones 10,11 and 12,13, in good yield and 80:20 d.r. After chromatographic separation, the configuration of pure diastereomers was assigned from 1H NMR data. The usefulness of this intramolecular cyclisation was proven by conversion of either 10 or 12 into pyrrolidin-2-one 14 which through simple steps gave (S)-3-pyrrolidineacetic acid, 2. Following the same synthetic scheme, but starting from either 11 or 13, (R)-3-pyrrolidineacetic acid 3 was obtained.

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Diastereomerically pure pyrrolidin-2-ones by intramolecular Michael reaction. Synthesis of both (S)- and (R)-3-pyrrolidineacetic acid

Abstract

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