Synthesis of Allenamides by Copper-Catalyzed Coupling of Propargylic Bromides and Nitrogen Nucleophiles

被引：22

作者：

Demmer, Charles S. ^{[1
]}

Benoit, Emeline ^{[1
]}

Evano, Gwilherm ^{[1
]}

机构：

[1] ULB, Lab Chim Organ, Serv Chim & PhysicoChim Organ, Ave FD Roosevelt 50,CP160-06, B-1050 Brussels, Belgium

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 06期

关键词：

ENANTIOSELECTIVE SYNTHESIS; NUCLEOSIDE ANALOGS; ROOM-TEMPERATURE; NATURAL-PRODUCTS; FACILE SYNTHESIS; CYCLIZATION; CYCLOADDITION; ALKYNYLATION; ACTIVATION; AMIDES;

D O I：

10.1021/acs.orglett.6b00372

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and general synthesis of allenamides derived from oxazolidinones and hydantoins is reported. Upon activation with a combination of a copper catalyst and a 2,2'-bipyridine derivative in the presence of an inorganic base, propargylic bromides were found to be suitable reagents for the direct allenylation of nitrogen nucleophiles by a formal copper-catalyzed S(N)2' reaction. Besides the availability of the starting materials, notable features of this route to allenamides are its mild reaction conditions, the reaction being performed at room temperature in most cases, and its applicability to the preparation of mono-, di-, as well as trisubstituted allenamides.

引用

页码：1438 / 1441

页数：4

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