Synthesis of Aminocyclobutanes through Ring Expansion of N-Vinyl-β-Lactams

被引：30

作者：

Cheung, Lawrence L. W. ^{[1
]}

Yudin, Andrei K. ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 06期

基金：

加拿大自然科学与工程研究理事会;

关键词：

STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; CYCLOADDITIONS; PATHWAYS;

D O I：

10.1021/ol900118d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both eight-membered enamide rings and fused [4.2.0]aminocyclobutane-containing delta-lactams can be accessed from N-vinyl-beta-lactams. The eight-membered rings are made through a [3,3] sigmatropic rearrangement. At elevated temperature, the eight-membered lactam undergoes electrocyclization to furnish fused cyclobutane delta-lactams in a diastereoselective manner.

引用

页码：1281 / 1284

页数：4

共 32 条

[1] β-lactams as versatile synthetic intermediates for the preparation of heterocycles of biological interest [J].

Alcaide, B ;

Almendros, P .

CURRENT MEDICINAL CHEMISTRY, 2004, 11 (14) :1921-1949

[2]

Alcaide B, 2002, SYNLETT, P381

[3] Functionalized eight-membered lactams via [3,3] sigmatropic rearrangement of 2-azetidinone-tethered 1,5-dienes [J].

Alcaide, B ;

Rodríguez-Ranera, C ;

Rodríguez-Vicente, A .

TETRAHEDRON LETTERS, 2001, 42 (17) :3081-3083

[4] β-lactams:: Versatile building blocks for the stereoselective synthesis of non-β-lactam products [J].

Alcaide, Benito ;

Almendros, Pedro ;

Aragoncillo, Cristina .

CHEMICAL REVIEWS, 2007, 107 (11) :4437-4492

[5] SYNTHESIS AND ACTIVITY OF A POTENT N-METHYL-D-ASPARTIC ACID AGONIST, TRANS-1-AMINOCYCLOBUTANE-1,3-DICARBOXYLIC ACID, AND RELATED PHOSPHONIC AND CARBOXYLIC-ACIDS [J].

ALLAN, RD ;

HANRAHAN, JR ;

HAMBLEY, TW ;

JOHNSTON, GAR ;

MEWETT, KN ;

MITROVIC, AD .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (10) :2905-2915

[6] AN IMPROVED PREPARATION OF VINYL IODIDES [J].

BARTON, DHR ;

BASHIARDES, G ;

FOURREY, JL .

TETRAHEDRON LETTERS, 1983, 24 (15) :1605-1608

[7] Synthesis and photochemistry of 1-iodocyclohexene: Influence of ultrasound on ionic vs. radical behaviour [J].

Blaskovicova, Marika ;

Gaplovsky, Anton ;

Blasko, Jaroslav .

MOLECULES, 2007, 12 (02) :188-193

[8]

BROWN JM, 1973, J CHEM SOC CHEM COMM, P319

[9] Novel reaction pathways for 2-pyridone [4+4] photoadducts [J].

Chen, Peiling ;

Chen, Yanping ;

Carroll, Patrick J. ;

Sieburth, Scott McN. .

ORGANIC LETTERS, 2006, 8 (15) :3367-3370

[10]

CHIBA T, 1990, CHEM PHARM BULL, V38, P2335

← 1 2 3 4 →