期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 17, 期 9, 页码 2698-2703出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201003111
关键词
asymmetric synthesis; chirality; chirality transfer; diols; Wittig rearrangement
资金
- National Natural Science Foundation of China (NSFC) [20973051]
- Zhejiang Provincial Natural Science Foundation of China [Y4090139]
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.
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