Synthesis of functionalized 1-azaspirocyclic cyclopentanones using Bronsted acid or N-bromosuccinimide promoted ring expansions

被引：48

作者：

Dake, GR ^{[1
]}

Fenster, MDB ^{[1
]}

Hurley, PB ^{[1
]}

Patrick, BO ^{[1
]}

机构：

[1] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 17期

关键词：

D O I：

10.1021/jo0493572

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Azaspirocyclic ring systems are present in a variety of alkaloids. Functionalized 1-azaspirocyclopentanones (6, 7, 11, 12) can be efficiently constructed through semipinacol ring expansion reactions of 2-(1-hydroxycyclobutyl)-p-toluenesulfonylenamides (4) promoted by either a Bronsted acid ((S)-(+)-10-camphorsulfonic acid or HCI) or N-bromosuccinimide, an electrophilic bromine source. Reactions promoted by N-bromosuccinimide tend to proceed in higher yields (80-95%) and with greater diastereoselectivity (3:1-1:0) compared to those reactions promoted by a Bronsted acid. In addition, N-bromosuccinimide promoted reactions can produce a complementary stereochemical outcome compared to the reactions using Bronsted acid.

引用

页码：5668 / 5675

页数：8

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