Structurally novel Bi- and tricyclic β-lactams via [2+2] cycloaddition or radical reactions in 2-azetidinone-tethered enallenes and allenynes

被引：55

作者：

Alcaide, B ^{[1
]}

Almendros, P

Aragoncillo, C

机构：

[1] Univ Complutense Madrid, Fac Quim, Dept Quim Organ, Madrid 28040, Spain

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

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 21期

关键词：

D O I：

10.1021/ol034995c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Thermolysis of beta-lactam-tethered enallenyl alcohols gave tricyclic ring structures via a formal [2 + 2] cycloaddition of the alkene with the distal bond of the allene, while the tin-promoted radical cyclization in 2-azetidinone-tethered allenynes proceeded to provide bicyclic beta-lactams containing a medium-sized ring. The access to cyclization precursors was achieved by regio- and stereoselective metal-mediated carbonyl allenylation of 4-oxoazetidine-2-carbaldehydes in an aqueous environment.

引用

页码：3795 / 3798

页数：4

共 76 条

[1] Asymmetric synthesis of unusual fused tricyclic β-lactam structures via aza-cycloadditions/ring closing metathesis [J].

Alcaide, B ;

Almendros, P ;

Alonso, JM ;

Redondo, MC .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (04) :1426-1432

[2] Lewis acid-promoted intermolecular carbonyl-ene reaction of enantiopure 4-oxoazetidine-2-carbaldehydes.: Rapid entry to novel fused polycyclic β-lactams [J].

Alcaide, B ;

Almendros, P ;

Pardo, C ;

Rodríguez-Ranera, C ;

Rodríguez-Vicente, A .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (08) :3106-3111

[3] Recent advances in the stereocontrolled synthesis of bi- and tricyclic-β-lactams with non-classical structure [J].

Alcaide, B ;

Almendros, P .

CURRENT ORGANIC CHEMISTRY, 2002, 6 (03) :245-264

[4] Efficient entry to highly functionalized β-lactams by regio- and stereoselective 1,3-dipolar cycloaddition reaction of 2-azetidinone-tethered nitrones.: Synthetic applications [J].

Alcaide, B ;

Almendros, P ;

Alonso, JM ;

Aly, MF ;

Pardo, C ;

Sáez, E ;

Torres, MR .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :7004-7013

[5]

Alcaide B, 2002, CHEM-EUR J, V8, P3646, DOI 10.1002/1521-3765(20020816)8:16<3646::AID-CHEM3646>3.0.CO

[6]

2-M

[7]

Alcaide B, 2002, CHEM-EUR J, V8, P1719, DOI 10.1002/1521-3765(20020402)8:7<1719::AID-CHEM1719>3.0.CO

[8]

2-U

[9]

Alcaide B, 2002, SYNLETT, P381

[10] New domino transposition/intramolecular Diels-Alder reaction in monocyclic allenols: a general strategy for tricyclic compounds [J].

Alcaide, B ;

Almendros, P ;

Aragoncillo, C ;

Redondo, MC .

CHEMICAL COMMUNICATIONS, 2002, (14) :1472-1473

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