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

被引：57

作者：

Gao, Guang ^{[1
]}

Gu, Feng-Lei ^{[1
]}

Jiang, Jian-Xiong ^{[1
]}

Jiang, Kezhi ^{[1
]}

Sheng, Chun-Qi ^{[1
]}

Lai, Guo-Qiao ^{[1
]}

Xu, Li-Wen ^{[1
,2
]}

机构：

[1] Hangzhou Normal Univ, Key Lab Organosilicon Chem & Mat Technol, Minist Educ, Hangzhou 310012, Zhejiang, Peoples R China

[2] Chinese Acad Sci, State Key Lab Oxo Synth & Select Oxidat, Lanzhou Inst Chem Phys, Lanzhou 730000, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 09期

基金：

中国国家自然科学基金;

关键词：

asymmetric synthesis; chirality; chirality transfer; diols; Wittig rearrangement; 1,2-WITTIG REARRANGEMENT; DIPHOSPHINE LIGANDS; SYNTHETIC APPROACH; BENZYL ETHERS; ACETAL 1,2; BIOSYNTHESIS; CONSTRUCTION; CONVERSION; GLYCOSIDES; COMPLEXES;

D O I：

10.1002/chem.201003111

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：2698 / 2703

页数：6

共 51 条

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