Phosphine-catalyzed intramolecular γ-umpolung addition of α-aminoalkylallenic esters: facile synthesis of 3-carbethoxy-2-alkyl-3-pyrrolines

被引：26
|
作者：
Andrews, Ian P.
Blank, Brian R.
Kwon, Ohyun
机构：
来源：
CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 43期
关键词：
HIGHLY DIASTEREOSELECTIVE SYNTHESIS; DOUBLE-MICHAEL REACTIONS; 3+2 CYCLOADDITION; 4+2 ANNULATION; ALLENOATE ADDITIONS; IMINES; ALLENES; 2,3-BUTADIENOATES; DIHYDROPYRONES; HETEROCYCLES;
D O I：
10.1039/c2cc31347b
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An array of N-tosylated alpha-aminoalkylallenic esters was prepared and their cyclization under the influence of nucleophilic phosphine catalysts was explored. The alpha-aminoalkylallenic esters were prepared through aza-Baylis-Hillman reactions or novel DABCO-mediated decarboxylative rearrangements of allenylic carbamates. Conversion of these substrates to 3-carbethoxy-2-alkyl-3-pyrrolines was facilitated through Ph3P-catalyzed intramolecular gamma-umpolung addition.
引用
收藏
页码：5373 / 5375
页数：3
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