Neighboring Lithium-Assisted [1,2]-Wittig Rearrangement: Practical Access to Diarylmethanol-Based 1,4-Diols and Optically Active BINOL Derivatives with Axial and sp3-Central Chirality
Neighboring Lithium-Assisted [1,2]-Wittig Rearrangement: Practical Access to Diarylmethanol-Based 1,4-Diols and Optically Active BINOL Derivatives with Axial and sp3-Central Chirality
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DOI：
10.1002/chem.201003111
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发表时间：
2011-02-01
影响因子：
4.3
通讯作者：
Xu, Li-Wen
中科院分区：
文献类型：
--
作者：
Gao, Guang;Gu, Feng-Lei;Xu, Li-Wen
通过邻位锂促进的[1，2]-Wittig重排反应，发展了一种简便实用的合成有用的二芳基甲醇基1，4-二醇和手性纯的BINOL衍生的具有轴向和sp（3）中心手性的二醇的方法。手性转移过程在芳族醚取代基方面显示出广泛的底物范围，这允许获得具有优异的对映体选择性（> 99%对映体过量）和产率（84-96%）的广泛范围的手性1，1 '-联萘-2-α-芳基甲醇-2'-醇。这是一个很有吸引力的手性资源，可以用来设计和制备特殊的配体或催化剂。
A facile and practical methodology for the synthesis of synthetically useful diarylmethanol-based 1,4-diols and enantiomerically pure BINOL-derived diols with axial and sp(3)-central chirality has been developed through neighboring lithium-promoted [1,2]-Wittig rearrangement. The chirality transfer process shows a broad substrate scope in terms of the aromatic ether substituent, which allows access to a broad of range of chiral 1,1'-binaphthalene-2-alpha-arylmethanol-2'-ols with excellent enantioselectivities (> 99% enantiomeric excess) and yields (84-96%). This should be considered as an available and attractive chiral source to design and prepare privileged ligands or catalysts.