Metal-mediated carbonyl-1,3-butadien-2-ylation by 1,4-bis(methanesulfonyl)-2-butyne or 1,4-dibromo-2-butyne in aqueous media:: Asymmetric synthesis of 3-substituted 3-hydroxy-β-lactams

被引：43

作者：

Alcaide, B ^{[1
]}

Almendros, P ^{[1
]}

Rodríguez-Acebes, R ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 06期

关键词：

D O I：

10.1021/jo016247b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Metal-mediated 1,3-butadien-2-ylation reactions between 1,4-dibromo-2-butyne or 1,4-bis(methanesulfonyl)-2-butyne and optically pure azetidine-2,3-diones were investigated in aqueous media, offering a convenient asymmetric entry to the potentially bioactive 3-substituted 3-hydroxy-beta-lactam moiety. The diastereoselectivity of the addition reaction was controlled by the bulky chiral auxiliary at C4. However, while the regioselectivity of the process was full, the chemical yield of the addition was a function of the nature of both the metal reagent and the system solvent as well. In addition, 2-azetidinone-tethered 1,3-butadienes can easily be transformed into other functionalities via Diels-Alder reaction.

引用

页码：1925 / 1928

页数：4

共 40 条

[1]

Alcaide B, 2001, EUR J ORG CHEM, V2001, P2001

[2] 4-Oxoazetidine-2-carbaldehydes as useful building blocks in stereocontrolled synthesis [J].

Alcaide, B ;

Almendros, P .

CHEMICAL SOCIETY REVIEWS, 2001, 30 (04) :226-240

[3] Recent progress in the synthesis and reactivity of azetidine-2,3-diones. A review [J].

Alcaide, B ;

Almendros, P .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2001, 33 (04) :315-+

[4] Straightforward asymmetric entry to highly functionalized medium-sized rings fused to β-lactams via chemo- and stereocontrolled divergent radical cyclization of Baylis-Hillman adducts derived from 4-oxoazetidine-2-carbaldehydes [J].

Alcaide, B ;

Almendros, P ;

Aragoncillo, C .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (05) :1612-1620

[5] Rapid and stereocontrolled synthesis of racemic and optically pure highly functionalized pyrrolizidine systems via rearrangement of 1,3-dipolar cycloadducts derived from 2-azetidinone-tethered azomethine ylides [J].

Alcaide, B ;

Almendros, P ;

Alonso, JM ;

Aly, MF .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) :1351-1358

[6] Regio- and stereocontrolled metal-mediated carbonyl propargylation or allenylation of enantiomerically pure azetidine-2,3-diones:: Synthesis of highly functionalized 3-substituted 3-hydroxy-β-lactams [J].

Alcaide, B ;

Almendros, P ;

Aragoncillo, C .

ORGANIC LETTERS, 2000, 2 (10) :1411-1414

[7] Unusual reaction of azetidine-2,3-diones with primary amines.: Straightforward asymmetric synthesis of α-amino acid and peptide derivatives [J].

Alcaide, B ;

Almendros, P ;

Aragoncillo, C .

CHEMICAL COMMUNICATIONS, 2000, (09) :757-758

[8] SYNTHETIC STUDIES ON TABTOXIN - SYNTHESIS OF A NATURALLY-OCCURRING INHIBITOR OF GLUTAMINE-SYNTHETASE, TABTOXININE-BETA-LACTAM, AND ANALOGS [J].

BALDWIN, JE ;

OTSUKA, M ;

WALLACE, PM .

TETRAHEDRON, 1986, 42 (12) :3097-3110

[9]

Bear BR, 2001, ANGEW CHEM INT EDIT, V40, P821

[10] Synthesis of a six-carbon sialic acid using an indium-mediated coupling [J].

Chappell, MD ;

Halcomb, RL .

ORGANIC LETTERS, 2000, 2 (14) :2003-2005

← 1 2 3 4 →