Diastereoselectivity enhancement in the 1,3-cycloaddition of β-lactam aldehydes.: Application to the synthesis of enantiopure indolizidinone amino esters

被引：22

作者：

Alcaide, B ^{[1
]}

Almendros, P

Redondo, MC

Ruiz, MP

机构：

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

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 22期

关键词：

D O I：

10.1021/jo051402y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiopure alpha-alkoxy,beta-lactam acetaldehydes were prepared via the thiazole-based one-carbon homologation. The 1,3-dipolar cycloaddition reaction involving (alpha-alkoxy beta-lactam acetaldehyde-derived azomethine ylides gave with excellent diastereoselectivity highly functionalized 2-azetidinone-tethered prolines, which were directly used for the first preparation of azabicyclo[4.3.0]-nonane (indolizidinone) amino esters from beta-lactams.

引用

页码：8890 / 8894

页数：5

共 48 条

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