Catalytic Enantioselective Simultaneous Control of Axial Chirality and Central Chirality in Allenes,Chinese Journal of Chemistry

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Catalytic Enantioselective Simultaneous Control of Axial Chirality and Central Chirality in Allenes
Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 2018-03-15 , DOI: 10.1002/cjoc.201800090
Jianxin Dai ₁ , Xinyu Duan ₁ , Jing Zhou ₁ , Chunling Fu ₁ , Shengming Ma ₁

Affiliation

Chiral molecules, which may contain one or more different type(s) of stereocentres, such as central, axial, planar, and helical chiralities, etc., are indispensable in chemistry, pharmaceutical industry, and life science. Despite many advances for the preparation of chiral molecules usually with a single type of chirality have been realized, simultaneous construction of different types of chiralities is still a significant challenge. Here, we wish to report a protocol for preparation of chiral allenes with both central and axial chiralities via a catalytic asymmetric allenylation of different biologically or synthetically useful fluorinated or non‐fluorinated nucleophiles with readily available racemic allenes by using a single chiral ligand. An echoing between the central chirality and axial chirality for the enantioselectivity was observed. This strategy provides a general and practical approach to functionalized optically active allenes bearing both central and axial chiralities with an excellent enantioselectivity under mild conditions.

中文翻译：

烯键催化手性和中心手性的对映选择性同时控制

手性分子，可以包含一种或多种不同类型的立体中心，例如中心，轴向，平面和螺旋手性等是化学，制药工业和生命科学必不可少的。尽管已经实现了通常具有单一手性类型的手性分子的制备方面的许多进展，但是同时构建不同类型的手性仍然是一项重大挑战。在这里，我们希望报告一种通过使用单个手性配体通过不同的生物学或合成有用的氟化或非氟化亲核试剂与易于获得的外消旋艾伦的催化不对称烯丙基化来制备具有中心和轴向手性的手性艾伦的方案。观察到手性的中心手性和轴向手性之间的回声。

更新日期：2018-03-15

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