Kinetic resolution of (±)-2-methyl-1,2,3,4-tetrahydroquinoline and (±)-2-methylindoline

Краснов, В. П.; Левит, Г. Л.; Андреева, И. Н.; Grishakov, A. N.; Charushin, Valery N.; Чупахин, О. Н.

doi:10.1070/mc2002v012n01abeh001545

Cited by 35 publications

(9 citation statements)

References 3 publications

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“…Previously it was shown that these conditions were the best ones for the preparative process. [1][2][3] The mixtures of the diastereoisomeric amides were enriched with either (S,S)-diastereomer 7a (de 40%), 8a (de 53%) or 9a (de 19%). Individual (S,S)-diastereoisomers 7a and 8a of high diastereomeric excess (de >99.5% according to HPLC and 1 H NMR) were obtained Tetrahedron: Asymmetry by recrystallisation from hexane-EtOAc.…”

Section: Resultsmentioning

confidence: 99%

N-Phthaloyl-(S)-alanyl chloride as a chiral resolving agent for the kinetic resolution of heterocyclic amines

Краснов

Левит

Кодесс

et al. 2004

Tetrahedron: Asymmetry

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Section: Resultsmentioning

confidence: 99%

N-Phthaloyl-(S)-alanyl chloride as a chiral resolving agent for the kinetic resolution of heterocyclic amines

Краснов

Левит

Кодесс

et al. 2004

Tetrahedron: Asymmetry

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“…16 The reaction is depicted in Scheme 4. The acylation of racemic 2-methyl indoline 1a with 0.5 equiv of (S)-naproxen chloride in the absence of any tertiary amine resulted in the kinetic resolution with predominant formation of (S,S)-diastereoisomeric amide 8 (76% de).…”

Section: Chiral Reagentsmentioning

confidence: 99%

Routes toward enantiopure 2-substituted indolines: an overview

Anas

Kagan

2009

Tetrahedron: Asymmetry

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“…Krasnov 等 [9] 先后报道了以化合物 10 与 11 作为手性试剂, 与消旋体 2-甲基吲哚啉 7 发生酰化反应, 经过水解得到对映体 2-甲基吲哚啉(S)-9 [8] (76% ee)和 2-甲基吲哚啉(R)-9 (38% ee)的合成方法(Scheme 2). …”

Section: 化学拆分法unclassified

Recent Development on the Synthetic Methods of Chiral Indoline Derivatives

Zhang¹,

Qin²,

Duan³

et al. 2012

Chin. J. Org. Chem.

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The indoline skeletons, widely present in alkaloids and other products with diverse biological activities, which also have been considered as privileged structures due to their widespread use as building blocks and chiral auxiliaries in asymmetric synthesis. The importance of these motifs has determined that numerous synthetic multi-step strategies have been developed. Consequently, there has been a continuing interest in the development of efficient methods to obtain enantioenriched substituted indolines. A lot of methods have been introduced, including dynamic kinetic resolution, asymmetric reactions, asymmetric domino cascade reactions and other novel reactions. These methods have been reviewed. Keywords indoline; asymmetric; synthesis 吲哚及其衍生物是 Adolf von Baeyer 在 1866 年首次通过还原靛红而获得, 1883 年, Fescher 和 Jourdan 利用丙酮酸和 1-甲基苯腙合成吲哚, 并于次年证实其结构 [1] .吲哚啉结构作为一类具有生物活性的结构单元, 普遍存在于生物碱和其他天然产物中 , 如 vinblastine (1), strychnine (2), (-)-physostigmine (3), ajmalinne (4) [2] (图 1). 其中手性的 2-位取代和 2,3-位双取代的吲哚啉衍生物因其广泛存在性和较好的生物活性而备受关注, 如 Benzasttain E (5)、血管紧张素酶抑制剂 Pentopril (6) [3] (图 1). 此外, 吲哚啉作为手性辅助基也成功应用于有机不对称合成中 [4] .近十年有较多关于不对称合成和拆分吲哚啉衍生物的文献报道, 也有文章对其进行综述 [3,5] . 主要包括氢化还原、化学拆分、生物酶拆分、不对称合成、手性合成子策略和不对称的 Domino 串联反应等. 本文主要对合成手性吲哚啉衍生物的的方法加以概括. 先后报道了以化合物 10 与 11 作为手性试剂, 与消旋体 2-甲基吲哚啉 7 发生酰化反应, 经过水解得到对映体 2-甲基吲哚啉(S)-9 吲哚啉衍生物的动力学拆分动力学拆分是实现外消旋体拆分的一种有效方法[8] (76% ee)和 2-甲基吲哚啉(R)-9 (38% ee)的合成方法(Scheme 2). 10 AcOH 76% deBenzene, r.t. 1114) (Eq. 12).

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Kinetic resolution of (±)-2-methyl-1,2,3,4-tetrahydroquinoline and (±)-2-methylindoline

Cited by 35 publications

References 3 publications

N-Phthaloyl-(S)-alanyl chloride as a chiral resolving agent for the kinetic resolution of heterocyclic amines

N-Phthaloyl-(S)-alanyl chloride as a chiral resolving agent for the kinetic resolution of heterocyclic amines

Routes toward enantiopure 2-substituted indolines: an overview

Recent Development on the Synthetic Methods of Chiral Indoline Derivatives

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