Axial chirality in xanthene-4, 5-dicarboxamides: 1,9-stereocontrol mediated by remote interactions between conformationally constrained amide groups

被引：25

作者：

Clayden, J ^{[1
]}

Kenworthy, MN ^{[1
]}

Youssef, LH ^{[1
]}

Helliwell, M ^{[1
]}

机构：

[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 27期

关键词：

D O I：

10.1016/S0040-4039(00)00833-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tertiary 9,9-dimethylxanthene-4,5-dicarboxamides have a C-2-symmetric, axially chiral ground state due to remote interactions between the conformationally constrained tertiary amide substituents. Double ortholithiation-alkylation blocks amide rotation, and the 3,6-dialkylated products are chiral, existing as a pair of enantiomeric C-2-symmetric atropisomers. Double lateral lithiation-electrophilic quench introduces a pair of 1,9-related stereogenic centres-each under the control of one of the conformationally constrained amides-with complete diastereoselectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：5171 / 5175

页数：5

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