Synthesis of 5-Substituted 2-Pyrrolidinones by Coupling of Organozinc Reagents with Cyclic N -Acyliminium Ions

被引：1
|
作者：
Zaragoza-Galicia, Ivann [1 ]
Santos-Sanchez, Zaira A. [1 ]
Hidalgo-Mercado, Yazmin, I [1 ]
Olivo, Horacio F. [1 ]
Romero-Ortega, Moises [1 ]
机构：
[1] Univ Autonoma Estado Mexico, Fac Quim, Dept Quim Organ, Toluca 50180, Mexico
来源：
SYNTHESIS-STUTTGART | 2019年 / 51卷 / 24期
关键词：
N-acyliminium ions; organozinc reagents; coupling reactions; 5-allyl-2-pyrrolidinones; azabicyclic systems; STEREOSELECTIVE ADDITION; AMINO-ACIDS; CONCISE SYNTHESIS; DELTA-LACTAMS; INDOLIZIDINE; CYCLIZATIONS; DERIVATIVES; GENERATION; REDUCTION; CHEMISTRY;
D O I：
10.1055/s-0037-1610733
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A coupling reaction between cyclic N-acyliminium ions with organozinc reagents is described. The cyclic N-acyliminium ions, generated in situ from N-substituted-5-hydroxy-2-pyrrolidinones by treatment with boron trifluoride-diethyl ether complex or titanium tetrachloride, are trapped by the organozinc reagent, which is formed from an alkyl bromide in the presence of zinc in the same reaction medium. The N-substituted-5-allyl-2-pyrrolidinones generated using this method serve as versatile intermediates for the synthesis of azabicyclic systems with indolizidine and pyrroloazepinolizidine cores.
引用
收藏
页码：4650 / 4656
页数：7
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