Asymmetric synthesis of a chiral buckybowl, trimethylsumanene

被引：112

作者：

Higashibayashi, Shuhei ^{[1
]}

Sakurai, Hidehiro ^{[1
,2
]}

机构：

[1] Inst Mol Sci, Res Ctr Mol Scale Nanosci, Okazaki, Aichi 4448787, Japan

[2] PRESTO, Tokyo 1020075, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 27期

关键词：

D O I：

10.1021/ja802822k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first asymmetric synthesis of a chiral buckybowl, a C-3 symmetric (C)-8,13,18-trimethylsumanene (1), was achieved by employing a synthetic strategy that translates chirality at sp(3) centers into bowl chirality. The synthesis features a syn selective cyclotrimerization of an enantiopure halonorbornene derivative, tandem ring-opening/closing olefin metathesis reactions, and DDQ oxidation at low temperature. The bowl-to-bowl inversion energy of 1 was determined as 21.6 kcal/mol by circular dichroism spectra measurement.

引用

页码：8592 / +

页数：3

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