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

被引：14

作者：

Alcaide, B ^{[1
]}

Rodríguez-Ranera, C ^{[1
]}

Rodríguez-Vicente, A ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 17期

关键词：

D O I：

10.1016/S0040-4039(01)00391-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The thermally induced [3,3] sigmatropic (Cope) rearrangement of cis-beta -lactams 1 having alkenyl groups at both the C3 and C4 positions to yield new functionalized eight-membered lactams (tetrahydroazocinones) 2, in racemic as well as optically pure forms. is reported. This process involves a novel, concerted C3 C4 bond breakage of the beta -lactam nucleus helped by ring strain. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：3081 / 3083

页数：3

共 26 条

[1] General and efficient synthesis of β-lactams bearing a quinone moiety at N1, C3 or C4 positions [J].

Alcaide, B ;

Almendros, P ;

Salgado, NR .

TETRAHEDRON LETTERS, 2001, 42 (08) :1503-1505

[2] Thermally induced isomerization of cis-1,3,4-trisubstituted 2-azetidinones [J].

Alcaide, B ;

Almendros, P ;

Salgado, NR ;

Rodríguez-Vicente, A .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (14) :4453-4455

[3] Diastereoselective Baylis-Hillman reaction of 4-oxoazetidine-2-carbaldehydes:: rapid, stereocontrolled and divergent radical synthesis of highly functionalised β-lactams fused to medium rings [J].

Alcaide, B ;

Almendros, P ;

Aragoncillo, C .

CHEMICAL COMMUNICATIONS, 1999, (18) :1913-1914

[4] THE STEREOSELECTIVE PREPARATION OF MONO-BETA-LACTAMS AND BIS-BETA-LACTAMS BY THE 1,4-DIAZA 1,3-DIENE-ACID CHLORIDE CONDENSATION - SCOPE AND SYNTHETIC APPLICATIONS [J].

ALCAIDE, B ;

MARTINCANTALEJO, Y ;

PEREZCASTELLS, J ;

RODRIGUEZLOPEZ, J ;

SIERRA, MA ;

MONGE, A ;

PEREZGARCIA, V .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) :5921-5931

[5] NEW REACTIVITY PATTERNS OF THE BETA-LACTAM RING - TANDEM C3-C4 BOND BREAKAGE REARRANGEMENT OF 4-ACYL-3,3-DIMETHOXY-2-AZETIDINONES OR 4-IMINO-3,3-DIMETHOXY-2-AZETIDINONES PROMOTED BY SNCL2.2H2O [J].

ALCAIDE, B ;

MARTINCANTALEJO, Y ;

RODRIGUEZLOPEZ, J ;

SIERRA, MA .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) :4767-4770

[6] Stereoselective allylation of 4-oxoazetidine-2-carbaldehydes.: Application to the stereocontrolled synthesis of fused tricyclic β-lactams via intramolecular Diels-Alder reaction of 2-azetidinone-tethered trienes [J].

Alcaide, B ;

Almendros, P ;

Salgado, NR .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (11) :3310-3321

[7]

Anastassiou A. G, 1984, COMPREHENSIVE HETERO, V7, P709

[8]

[Anonymous], 1958, Justus Liebigs Ann. Chem

[9] FORMATION AND THERMAL REARRANGEMENTS OF SOME DIMERS OF BUTADIENE AND PIPERYLENE - TESTS OF VALIDITY OF THERMOCHEMICAL-KINETIC ARGUMENTS FOR IDENTIFICATION OF COMMON BIRADICAL INTERMEDIATES [J].

BERSON, JA ;

DERVAN, PB ;

MALHERBE, R ;

JENKINS, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (19) :5937-5968

[10] FURTHER OBSERVATIONS ON REARRANGEMENT OF 3-ACYLAMINOAZETIDINONES [J].

BIRD, CW ;

TWIBELL, JD .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (19) :3155-&

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