Asymmetric control in Diels-Alder cycloadditions of chiral 9-aminoanthracenes by relay of stereochemical information

被引：28

作者：

Adams, Harry ^{[1
]}

Bawa, Ramadan A. ^{[1
]}

McMillan, Keith G. ^{[1
]}

Jones, Simon ^{[1
]}

机构：

[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

来源：

TETRAHEDRON-ASYMMETRY | 2007年 / 18卷 / 08期

关键词：

D O I：

10.1016/j.tetasy.2007.04.012

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Two approaches to the synthesis of chiral 9-amino anthracenes are described. The first, by nucleophilic addition of organolithium reagents to imines promoted by BF3 center dot OEt2, unexpectedly provided stable aminoboranes as products. The second approach, using palladium catalysed cross coupling, was more successful for primary amines, and the key 9-(alpha-methylbenzylamino)anthracene subjected to cycloadditions with N-methyl maleimide and maleic anhydride. Excellent reactivity was achieved with good levels of diastereoselectivity, through a favourable combination of electrostatic and hydrogen bonding effects. Trial studies of the retro Diels-Alder reaction of these cycloadducts were also performed. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：1003 / 1012

页数：10

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