Multimilligram‐scale production implementation of atropisomers of 2,2′‐bis(2,2′‐bithiophene‐5‐yl)‐3,3′‐bithianaphthene,Chirality

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Multimilligram‐scale production implementation of atropisomers of 2,2′‐bis(2,2′‐bithiophene‐5‐yl)‐3,3′‐bithianaphthene
Chirality ( IF 2.8 ) Pub Date : 2021-02-14 , DOI: 10.1002/chir.23294
Alessia Rosetti _{1,

2} , Giorgia Bonetti ₃ , Claudio Villani ₂ , Tiziana Benincori ₃ , Roberto Cirilli ₁

Affiliation

2,2′‐Bis[2‐(5,2′‐bithienyl)]‐3,3′‐bithianaphthene (1) is the progenitor of a class of C₂ symmetric thiophene‐based electroactive monomers that, when electrooxidized in the enantiomerically pure form, produce inherently chiral films endowed with outstanding electrochemical enantiorecognition properties. The enantioselective high‐performance liquid chromatography (HPLC) is the only approach used so far to resolve the racemic form of 1 into enantiomers. In this work, an improved HPLC method for multimilligram enantiomer production is presented. Key factors controlling the enantioseparation, such as mobile phase composition and column temperature, were identified using a 100 × 4.6 mm i.d. Chiralpak IB‐3 column and subsequently scaled up to a 250 × 10.0 mm i.d. Chiralpak IB column. In the optimized semipreparative conditions, about 34 mg of pure (P) and (M) enantiomers per hour could be produced.

中文翻译：

2,2'-双（2,2'-联噻吩-5-基）-3,3'-联萘的阻转异构体的毫克级生产实施

2,2'-Bis [2-（5,2'-噻吩基）]-3,3'-联萘（1）是一类基于C ₂对称噻吩的电活性单体的祖先，当在对映体中被电氧化时纯净的形式，可生产具有出色的电化学对映体识别特性的内在手性薄膜。对映选择性高效液相色谱法（HPLC）是迄今为止用于解决1的外消旋形式的唯一方法成对映体。在这项工作中，提出了一种改进的HPLC方法，用于生产毫克对映体。使用100×4.6 mm内径的Chiralpak IB-3色谱柱确定了控制对映体分离的关键因素，例如流动相组成和色谱柱温度，随后放大至250×10.0 mm内径的Chiralpak IB色谱柱。在优化的半制备条件下，每小时可生产约34 mg的纯（P）和（M）对映体。

更新日期：2021-03-09

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