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.
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-α-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.
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou, P R China.
Guang
G
Gao
Feng-Lei
FL
Gu
Jian-Xiong
JX
Jiang
Kezhi
K
Jiang
Chun-Qi
CQ
Sheng
Guo-Qiao
GQ
Lai
Li-Wen
LW
Xu