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
作者:Guang Gao、Feng-Lei Gu、Jian-Xiong Jiang、Kezhi Jiang、Chun-Qi Sheng、Guo-Qiao Lai、Li-Wen Xu
DOI:10.1002/chem.201003111
日期:2011.2.25
synthetically useful diarylmethanol‐based 1,4‐diols and enantiomerically pure BINOL‐derived diols with axial and sp3‐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‐α‐arylmethanol‐2′‐ols
通过相邻的锂促进的[1,2] -Wittig重排,已开发出一种简便实用的方法来合成合成有用的基于二芳基甲醇的1,4-二醇和对映体纯的BINOL衍生的具有轴向和sp 3中心手性的二醇。。手性转移过程显示出在芳香族醚取代基方面广泛的底物范围,从而可以得到具有出色对映选择性(> 99的手性1,1'-联萘-2-α-芳基甲醇-2'-醇)的广泛范围。对映体过量百分比)和收率(84–96%)。这应该被认为是设计和制备优先的配体或催化剂的可用且有吸引力的手性来源。