Expeditious Entry to Enantiopure Mono- and Bis(Tricyclic) β-Lactams by Single or Double [2+2] Cycloaddition of Allenynes

被引：15

作者：

Alcaide, Benito ^{[1
]}

Almendros, Pedro ^{[2
]}

Aragoncillo, Cristina ^{[1
]}

Gomez-Campillos, Gonzalo ^{[1
]}

机构：

[1] Univ Complutense Madrid, Grp Lactamas & Heterociclos Bioact, Dept Quim Organ 1, Unidad Asociada CSIC,Fac Quim, E-28040 Madrid, Spain

[2] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 02期

关键词：

Allenes; Alkynes; Cyclization; Lactams; Radicals; Small ring systems; STEREOCONTROLLED SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; CYCLOBUTANE DERIVATIVES; ALPHA-ALLENOLS; GAMMA-ALLENOLS; 4-OXOAZETIDINE-2-CARBALDEHYDES; CHEMISTRY; REGIOSELECTIVITY; CONSTRUCTION; CYCLIZATIONS;

D O I：

10.1002/ejoc.201001233

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A thermal methodology for the expeditious preparation of structurally novel strained tricyclic beta-lactams containing a cyclobutene ring has been developed. Besides, the first examples accounting for the intramolecular double [2+2] cycloaddition of bis(allenyne)s have been achieved through thermolysis of C-2-symmetric or unsymmetric bis(beta-lactam-allenyne)s, which have been prepared by copper-promoted alkyne homo- or cross-coupling reactions. The bis(tricyclic) ring structures bearing a central seven-membered ring arise from the regioselective cyclization of the alkyne with the distal bond of the allene, most likely via a radical intermediate.

引用

页码：364 / 370

页数：7

共 62 条

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