Asymmetric synthesis of trans-3-amino-4-alkylazetidin-2-ones from chiral N,N-dialkylhydrazones

被引：34

作者：

Díez, E

Fernández, R

Marqués-López, E

Martín-Zamora, E

Lassaletta, JM

机构：

[1] Univ Sevilla, Dept Quim Organ, Fac Quim, E-41071 Seville, Spain

[2] USe, CSIC, Inst Invest Quimicas, E-41092 Seville, Spain

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 16期

关键词：

D O I：

10.1021/ol0490328

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiopure N,N-dialkylhydrazones 3 smoothly react with N-benzyloxycarbonyl-N-benzyl glycine as an aminoketene precursor to afford trans-3-amino-4-alkylazetidin-2-ones 4 as single diasteromers. As an exception, hydrazone 3f (R = OBn) affords cis-(3R,4R)-4f under modified conditions. N-N Bond cleavage of cycloadducts 4 afforded free azetidinones 5 in high yields.

引用

页码：2749 / 2752

页数：4

共 17 条

[1] THE ASYMMETRIC-SYNTHESIS OF BETA-LACTAM ANTIBIOTICS .1. APPLICATION OF CHIRAL OXAZOLIDONES IN THE STAUDINGER REACTION [J].