Carbamate-directed benzylic lithiation for the diastereo- and enantioselective synthesis of diaryl ether atropisomers

被引：15
作者：
Page, Abigail [1 ]
Clayden, Jonathan [1 ]
机构：
[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 7卷
基金：
英国工程与自然科学研究理事会;
关键词：
configurational stability; diaryl ether; diastereoselective; enantioselective; lateral lithiation; metallation; ASYMMETRIC-SYNTHESIS; DYNAMIC RESOLUTION; AMIDES; N; N'-DIARYLUREAS; RACEMIZATION; STABILITY; REAGENTS; LIGANDS; BONDS;
D O I：
10.3762/bjoc.7.156
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Diaryl ethers carrying carbamoyloxymethyl groups may be desymmetrised enantio- and diastereoselectively by the use of the secBuLi-(-)- sparteine complex in diethyl ether. Enantioselective deprotonation of one of the two benzylic positions leads to atropisomeric products with ca. 80: 20 e.r.; an electrophilic quench typically provides functionalised atropisomeric diastereoisomers in up to 97:3 d.r.
引用
收藏
页码：1327 / 1333
页数：7
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