Synthesis of optically active 1,5-benzothiazepines

Lévai, Albert; Kiss‐Szikszai, Attila

doi:10.3998/ark.5550190.0009.103

Arkivoc

2008

DOI: 10.3998/ark.5550190.0009.103

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Synthesis of optically active 1,5-benzothiazepines

Albert Lévai¹,

Attila Kiss‐Szikszai²

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Cited by 25 publications

(1 citation statement)

References 39 publications

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“… Thus, the development of efficient and enantioselective synthetic approaches to diverse 1,5-benzothiazepine derivatives is of great importance for drug discovery. Although a number of synthetic methods to construct this framework have been documented, , catalytic asymmetric synthesis is still challenging. Recently, Matsubara and Glorius developed two different efficient approaches to enantioenriched N -substituted 1,5-benzothiazepines via an organocatalytic [4 + 3] cycloaddition and transition-metal-catalytic hydrogenation, respectively.…”

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confidence: 99%

Formal [3 + 4] Annulation of α,β-Unsaturated Acyl Azoliums: Access to Enantioenriched N–H-Free 1,5-Benzothiazepines

et al. 2017

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An unprecedented formal [3 + 4] annulation of α,β-unsaturated acyl azoliums with 2-aminobenzenethiols has been utilized to synthesize enantioenriched N-H-free 1,5-benzothiazepines, which are recognized as privileged structures in numerous biologically active scaffolds. This protocol offers a rapid and direct pathway to access the target compounds with high enantioselectivities and has been applied in the concise synthesis of chiral drug (R)-thiazesim.

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confidence: 99%

Formal [3 + 4] Annulation of α,β-Unsaturated Acyl Azoliums: Access to Enantioenriched N–H-Free 1,5-Benzothiazepines

et al. 2017

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Catalytic Asymmetric Conjugate Addition of Thiols to α,β‐Unsaturated Thioamides: Expeditious Access to Enantioenriched 1,5‐Benzothiazepines

2012

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Conjugate addition offers a general strategy for site-specific reactions at carbon-carbon double bonds and is frequently used in organic synthesis. Recent advances in this field have rendered the transformation viable in both a catalytic and asymmetric manner. Although a wide variety of carbon and heteroatom nucleophiles are used in this process, [1][2][3][4][5] the range of electrophiles used has been mostly limited to highly electrophilic conjugate addition acceptors, such as enones, enals, and nitroolefins. a,b-Unsaturated carboxylic acid derivatives exhibit inherently lower electrophilicity at the bcarbon atom and are thus less-common substrates in catalytic asymmetric conjugate addition reactions. We recently found that soft Lewis acids enhance the electrophilicity of a,bunsaturated thioamides 1, thus making them amenable to conjugate addition with in situ generated carbon nucleophiles. [6] To expand the scope of conjugate additions using a thioamide electrophiles, we envisioned that the use of a soft Lewis basic heteroatom nucleophile would preferentially produce an electrophile and nucleophile assembly in an asymmetric environment at the transition state, thereby affording the enantioenriched conjugate-addition product. Herein, we report a catalytic asymmetric conjugate addition (sulfa-Michael reaction) of thiols 2, as a soft nucleophile, to a,b-unsaturated thioamides 1 (Scheme 1). [5,7,8] Optically active sulfides have a wide range of applications in chemistry and biology as chiral auxiliaries, ligands for asymmetric catalysis, and biologically active compounds.

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Asymmetrische Hydrierung von Vinylthioethern: Zugang zu optisch aktiven 1,5‐Benzothiazepinderivaten

Schlepphorst

Daniliuc

et al. 2016

Angewandte Chemie

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Eine neuartige asymmetrische Hydrierung von Vinylthioethern unter Verwendung eines Ruthenium(II)‐NHC‐Komplexes ermöglicht die effiziente Herstellung optisch aktiver 1,5‐Benzothiazepine mit C‐S‐Bindungen am Stereozentrum. Exzellente Enantioselektivitäten (bis zu 95 % ee) und hohe Ausbeuten (bis zu 99 %) wurden für eine Vielzahl von Substraten mit nützlichen funktionellen Gruppen erhalten. Außerdem konnte diese Methode bei der Synthese des Antidepressivums R‐(−)‐Thiazesim angewendet werden.

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Synthesis of optically active 1,5-benzothiazepines

Cited by 25 publications

References 39 publications

Formal [3 + 4] Annulation of α,β-Unsaturated Acyl Azoliums: Access to Enantioenriched N–H-Free 1,5-Benzothiazepines

Formal [3 + 4] Annulation of α,β-Unsaturated Acyl Azoliums: Access to Enantioenriched N–H-Free 1,5-Benzothiazepines

Catalytic Asymmetric Conjugate Addition of Thiols to α,β‐Unsaturated Thioamides: Expeditious Access to Enantioenriched 1,5‐Benzothiazepines

Asymmetrische Hydrierung von Vinylthioethern: Zugang zu optisch aktiven 1,5‐Benzothiazepinderivaten

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