Intramolecular [3+2] annulation of olefin-tethered cyclopropylamines

被引：72

作者：

Ha, JD ^{[1
]}

Lee, JW ^{[1
]}

Blackstock, SC ^{[1
]}

Cha, JK ^{[1
]}

机构：

[1] Univ Alabama, Dept Chem, Tuscaloosa, AL 35487 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 23期

关键词：

D O I：

10.1021/jo9817671

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Starting from readily available olefin-tethered tertiary aminocyclopropanes, we have developed a convenient [3 + 2] annulation reaction by means of one-electron oxidation which can be induced photochemically or chemically, followed by two sequential 5-exo radical cyclizations. The rate constants for the competing 1,5-hydrogen transfer in the beta-immonium carbon radical intermediate have been estimated to fall between 1000 (6-exo) and 100 (7-exo and/or 8-endo) s(-1) at room temperature.

引用

页码：8510 / 8514

页数：5

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