Synthesis of Inherently Chiral Calix[4]arenes: Stereocontrol through Ligand Choice

被引:44
|
作者
Herbert, Simon A. [1 ]
Arnott, Gareth E. [1 ]
机构
[1] Univ Stellenbosch, Dept Chem & Polymer Sci, ZA-7602 Matieland, South Africa
关键词
HEXAMETHYLPHOSPHORAMIDE HMPA; LITHIUM DIISOPROPYLAMIDE; LITHIATION; BUTYLLITHIUM; COMPLEXES; MECHANISM; BEHAVIOR; SOLVENT; DIMERS;
D O I
10.1021/ol101909f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Employing a chiral oxazoline as an ortholithiation directing group allows the synthesis of inherently chiral calix[4]arenes suitable for elaboration into planar chiral molecules. An important finding has been that the diastereoselectivity of the reaction can be tuned by the choice of additive These results have bearing on the elucidation of the general mechanism of oxazoline-directed ortholithiation
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页码:4600 / 4603
页数:4
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