Heteroaromatic Synthesis via Olefin Cross-Metathesis: Entry to Polysubstituted Pyridines

被引：70

作者：

Donohoe, Timothy J. ^{[1
]}

Basutto, Jose A. ^{[1
]}

Bower, John F. ^{[1
]}

Rathi, Akshat ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 05期

基金：

英国工程与自然科学研究理事会;

关键词：

RING-CLOSING METATHESIS; HIGHLY FUNCTIONALIZED PYRIDINES; METHOXY-N-METHYLAMIDES; ONE-POT SYNTHESIS; DIRECT ARYLATION; SUBSTITUTED PYRIDINES; HALOGENATED NITROGEN; AROMATIC-COMPOUNDS; (R)-(+)-MUSCOPYRIDINE; HETEROCYCLES;

D O I：

10.1021/ol103088r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The olefin cross-metathesis reaction provides a rapid and efficient method for the synthesis of alpha,beta-unsaturated 1,5-dicarbonyl derivatives which then serve as effective precursors to mono-tetrasubstituted pyridines. Manipulation of the key 1,5-dicarbonyl intermediate allows access to pyridines with a wide range of substitution patterns. An extension of this methodology facilitates the preparation of pyridines embedded within macrocycles, as exemplified by an efficient synthesis of (R)-(+)-muscopyridine. High levels of regiocontrol, short reaction sequences, and facile substituent variation are all notable aspects of this methodology.

引用

页码：1036 / 1039

页数：4

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