SYNTHESIS OF THE HELICOPODANDS - NOVEL SHAPES FOR CHIRAL CLEFTS

被引：70

作者：

DESHAYES, K ^{[1
]}

BROENE, RD ^{[1
]}

CHAO, I ^{[1
]}

KNOBLER, CB ^{[1
]}

DIEDERICH, F ^{[1
]}

机构：

[1] UNIV CALIF LOS ANGELES,DEPT CHEM & BIOCHEM,LOS ANGELES,CA 90024

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 24期

关键词：

D O I：

10.1021/jo00024a017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Helicopodands are a new class of chiral nonmacrocyclic ("podand") receptors with a helicene backbone ("helico"). At the termini of the helix, they form a preorganized cleft of pronounced asymmetric character which is aligned with convergent hydrogen bonding functionality. The synthetic routes to the two helicopodands 2 and 3 each include two photocyclodehydrogenation reactions. The X-ray crystal structure of 14, a direct helical precursor to 2 and 3, confirms the main structural features of the helicopodands. MMP2 calculations give a geometric description of 14 which is in reasonable agreement with the X-ray results.

引用

页码：6787 / 6795

页数：9

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