Straightforward Enantioselective Access to γ-Butyrolactones Bearing an All-Carbon β-Quaternary Stereocenter

被引：24
|
作者：
Meninno, Sara [1 ]
Fuoco, Tiziana [1 ]
Tedesco, Consiglia [1 ]
Lattanzi, Alessandra [1 ]
机构：
[1] Univ Salerno, Dipartimento Chim & Biol, I-84084 Fisciano, Italy
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 18期
关键词：
ASYMMETRIC ALDOL REACTION; BAEYER-VILLIGER REACTION; STEREOSELECTIVE CONSTRUCTION; MICHAEL ADDITION; ORGANOCATALYSIS; FORMALDEHYDE; TETRAHYDROFURAN; CYCLOBUTANONES; ESTERS;
D O I：
10.1021/ol502148a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An enantioselective one-pot aldol/lactonization sequence has been developed to access highly challenging gamma-butyrolactones bearing an all-carbon quaternary stereocenter at the beta-position by reacting acylated succinic esters with aqueous formaldehyde in the presence of 3 mol 96 loading of a cinchona alkaloid-derived squaramide providing direct access to paraconic acid derivatives in high yield and fairly good level of enantioselectivity (up to 88% ee).
引用
收藏
页码：4746 / 4749
页数：4
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