Novel N1-C4 β-lactam bond breakage.: Synthesis of enantiopure α-alkoxy-γ-keto acid derivatives

被引：22

作者：

Alcaide, B ^{[1
]}

Almendros, P

Redondo, MC

机构：

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

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

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 11期

关键词：

D O I：

10.1021/ol049549j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Addition reaction of 2-(trimethylsilyl)thiazole (TMST) to cis- or trans-4-formyl-beta-lactams gave enantiopure alpha-alkoxy-gamma-keto acid derivatives via a novel N1-C4 bond breakage of the beta-lactam nucleus. This is the first time that the cleavage of the N1-C4 bond on the beta-lactam nucleus has been shown to occur in 2-azetidinones lacking an aryl moiety at C4.

引用

页码：1765 / 1767

页数：3

共 25 条

[21]

2-F

[22] Asymmetric synthesis of building-blocks for peptides and peptidomimetics by means of the beta-lactam synthon method [J].

Ojima, I ;

Delaloge, F .

CHEMICAL SOCIETY REVIEWS, 1997, 26 (05) :377-386

[23] RECENT ADVANCES IN THE BETA-LACTAM SYNTHON METHOD [J].

OJIMA, I .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (09) :383-389

[24]

Palomo C, 2001, SYNLETT, P1813

[25] STUDIES ON LACTAMS .81. ENANTIOSPECIFIC SYNTHESIS AND ABSOLUTE-CONFIGURATION OF SUBSTITUTED BETA-LACTAMS FROM D-GLYCERALDEHYDE ACETONIDE [J].

WAGLE, DR ;

GARAI, C ;

CHIANG, J ;

MONTELEONE, MG ;

KURYS, BE ;

STROHMEYER, TW ;

HEGDE, VR ;

MANHAS, MS ;

BOSE, AK .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18) :4227-4236

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