e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Tetrahedron: Asymmetry

Enantioselective synthesis of (R)-(−)-baclofen via Ru (II)–BINAP catalyzed asymmetric hydrogenation

VV Thakur, MD Nikalje, A Sudalai

Index: Thakur, Vinay V.; Nikalje, Milind D.; Sudalai Tetrahedron Asymmetry, 2003 , vol. 14, # 5 p. 581 - 586

Full Text: HTML

Citation Number: 46

Abstract

A short and efficient enantioselective synthesis of (R)-(−)-baclofen, a selective GABAB agonist has been described with an overall yield of 26% and 90% ee. Ru (II)–(S)-BINAP catalyzed asymmetric hydrogenations of C C and C O groups constitute the key steps in introducing stereogenic centers into the molecule.

ethyl (2E)-3-(4'-chlorophenyl)but-2-enoate Structure

ethyl (2E)-3-(4...

~92%

ethyl 4-bromo-3-(4-chlorophenyl)but-2-enoate Structure

ethyl 4-bromo-3...

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ethyl 3-(4-chlorophenyl)-3-hydroxybutanoate Structure

ethyl 3-(4-chlo...

~%

ethyl 4-bromo-3-(4-chlorophenyl)but-2-enoate Structure

ethyl 4-bromo-3...

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1-(4-Chlorophenyl)ethanone Structure

1-(4-Chlorophen...

~%

ethyl 4-bromo-3-(4-chlorophenyl)but-2-enoate Structure

ethyl 4-bromo-3...

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ethyl 4-azido-3-(4-chlorophenyl)-2-butenoate Structure

ethyl 4-azido-3...

~%

(R)-Baclofen (hydrochloride) Structure

(R)-Baclofen (h...

(S)-Baclofen hydrochloride Structure

(S)-Baclofen hy...

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ethyl 3-(4-chlorophenyl)-3-hydroxybutanoate Structure

ethyl 3-(4-chlo...

~%

(R)-Baclofen (hydrochloride) Structure

(R)-Baclofen (h...

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ethyl (2E)-3-(4'-chlorophenyl)but-2-enoate Structure

ethyl (2E)-3-(4...

~%

(R)-Baclofen (hydrochloride) Structure

(R)-Baclofen (h...

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1-(4-Chlorophenyl)ethanone Structure

1-(4-Chlorophen...

~%

(R)-Baclofen (hydrochloride) Structure

(R)-Baclofen (h...

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ethyl 4-bromo-3-(4-chlorophenyl)but-2-enoate Structure

ethyl 4-bromo-3...

~%

(R)-Baclofen (hydrochloride) Structure

(R)-Baclofen (h...

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Ethyl 3-(4-chlorophenyl)-3-oxopropanoate Structure

Ethyl 3-(4-chlo...

~%

(R)-Baclofen (hydrochloride) Structure

(R)-Baclofen (h...

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ethyl (3R)-3-cyano-3-(4-chlorophenyl)propanoate Structure

ethyl (3R)-3-cy...

~%

(R)-Baclofen (hydrochloride) Structure

(R)-Baclofen (h...

(S)-Baclofen hydrochloride Structure

(S)-Baclofen hy...

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Ethyl 3-(4-chlorophenyl)-3-hydroxypropanoate Structure

Ethyl 3-(4-chlo...

~77%

Ethyl 3-(4-chlorophenyl)-3-oxopropanoate Structure

Ethyl 3-(4-chlo...

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ethyl 4-azido-3-(4-chlorophenyl)-2-butenoate Structure

ethyl 4-azido-3...

~%

(R)-Baclofen (hydrochloride) Structure

(R)-Baclofen (h...

(S)-Baclofen hydrochloride Structure

(S)-Baclofen hy...

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ethyl 3-(4-chlorophenyl)-3-hydroxybutanoate Structure

ethyl 3-(4-chlo...

~%

(S)-Baclofen hydrochloride Structure

(S)-Baclofen hy...

Learn More

ethyl (2E)-3-(4'-chlorophenyl)but-2-enoate Structure

ethyl (2E)-3-(4...

~%

(S)-Baclofen hydrochloride Structure

(S)-Baclofen hy...

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1-(4-Chlorophenyl)ethanone Structure

1-(4-Chlorophen...

~%

(S)-Baclofen hydrochloride Structure

(S)-Baclofen hy...

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ethyl 4-bromo-3-(4-chlorophenyl)but-2-enoate Structure

ethyl 4-bromo-3...

~%

(S)-Baclofen hydrochloride Structure

(S)-Baclofen hy...

Learn More

Ethyl 3-(4-chlorophenyl)-3-oxopropanoate Structure

Ethyl 3-(4-chlo...

~%

(S)-Baclofen hydrochloride Structure

(S)-Baclofen hy...

Learn More

ethyl (3R)-3-cyano-3-(4-chlorophenyl)propanoate Structure

ethyl (3R)-3-cy...

~%

(R)-Baclofen (hydrochloride) Structure

(R)-Baclofen (h...

(S)-Baclofen hydrochloride Structure

(S)-Baclofen hy...

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