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

页码：4650 / 4656

页数：7

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