cheminform abstract: optically active 1,5-benzothiazepin-4-ones by ring transformation of...

2000 multi-membered O,N,S-heterocycles multi-membered O,N,S-heterocycles (with at least 2 diﬀerent heteroatoms) R 0692 41 - 134 Optically Active 1,5-Benzothiazepin-4-ones by Ring Transformation of 5-Ylidene-1,3-dioxan-4-ones with 2-Aminothiophenol. — The synthesis of title optically active benzothiazepinones (IV) and (VII) is presented, involving the stereoselective conjugate addition of o-aminothiophenol (II) to enantiomeric E- (I) or Z-ylidenedioxanones (V). This Michael addition provides diastereomeric mixtures of compounds (III) and (VI) with trans-adduct (III) predominating from addition to the E-isomer (I) and vice versa. The mechanism and mode of selectivity of this addition reaction is discussed. Ring closure to the corresponding benzothiazepinones is then smoothly achieved by activation of the free amino group with EtMgBr. — (ALI, AKBAR; AHMAD, VIQAR UDDIN; LEISTNER, JOACHIM; LIEBSCHER, JUERGEN; Perkin 1 (2000) 12, 1897-1902; Inst. Chem., Humboldt-Univ., D-10115 Berlin, Germany; EN) 1

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Page 1: ChemInform Abstract: Optically Active 1,5-Benzothiazepin-4-ones by Ring Transformation of 5-Ylidene-1,3-dioxan-4-ones with 2-Aminothiophenol

2000 multi-membered O,N,S-heterocycles

multi-membered O,N,S-heterocycles (with at least 2 different heteroatoms)R 0692

41 - 134Optically Active 1,5-Benzothiazepin-4-ones by Ring Transformationof 5-Ylidene-1,3-dioxan-4-ones with 2-Aminothiophenol. — Thesynthesis of title optically active benzothiazepinones (IV) and (VII) is presented,involving the stereoselective conjugate addition of o-aminothiophenol (II) toenantiomeric E- (I) or Z-ylidenedioxanones (V). This Michael addition providesdiastereomeric mixtures of compounds (III) and (VI) with trans-adduct (III)predominating from addition to the E-isomer (I) and vice versa. The mechanismand mode of selectivity of this addition reaction is discussed. Ring closure tothe corresponding benzothiazepinones is then smoothly achieved by activationof the free amino group with EtMgBr. — (ALI, AKBAR; AHMAD, VIQARUDDIN; LEISTNER, JOACHIM; LIEBSCHER, JUERGEN; Perkin 1 (2000)12, 1897-1902; Inst. Chem., Humboldt-Univ., D-10115 Berlin, Germany; EN)

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