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
Ojima, I
Delaloge, F
[J]. CHEMICAL SOCIETY REVIEWS, 1997, 26 (05) : 377 - 386
[23] RECENT ADVANCES IN THE BETA-LACTAM SYNTHON METHOD
OJIMA, I
[J]. 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
WAGLE, DR
GARAI, C
CHIANG, J
MONTELEONE, MG
KURYS, BE
STROHMEYER, TW
HEGDE, VR
MANHAS, MS
BOSE, AK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18) : 4227 - 4236

← 1 2 3 →