Enantioselective synthesis of α,α-difluoro-β-lactams using amino alcohol ligands

被引：17
|
作者：
Tarui, Atsushi [1 ]
Ikebata, Takeshi [1 ]
Sato, Kazuyuki [1 ]
Omote, Masaaki [1 ]
Ando, Akira [1 ]
机构：
[1] Setsunan Univ, Fac Pharmaceut Sci, Hirakata, Osaka 5730101, Japan
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 33期
关键词：
DIFLUORO-BETA-LACTAMS; REFORMATSKY-TYPE REACTION; HUMAN-LEUKOCYTE ELASTASE; ASYMMETRIC-SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; ETHYL BROMODIFLUOROACETATE; STEREOSELECTIVE-SYNTHESIS; ESTERS; CHEMISTRY; FLUORINE;
D O I：
10.1039/c4ob01184h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A practical and highly enantioselective Reformatsky reaction of ethyl bromodifluoroacetate with imines using a cheap and commercially available amino alcohol ligand is described. A variety of alpha,alpha-difluoro-beta-lactams were obtained in up to 74% yield with high enantioselectivity in excess of 99% ee. The use of ethyl bromodifluoroacetate provides for ease of operation because of the inherent chemical stability of this reagent.
引用
收藏
页码：6484 / 6489
页数：6
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