Synthesis of Lactones and Lactams from Vinylcyclopropane by Palladium-Catalyzed Nucleophilic Allylation

被引：9
|
作者：
Hirata, Goki [1 ]
Onodera, Gen [1 ]
Kimura, Masanari [1 ]
机构：
[1] Nagasaki Univ, Grad Sch Engn, Nagasaki 8528521, Japan
来源：
SYNLETT | 2014年 / 25卷 / 16期
关键词：
palladium; vinylcyclopropane; nucleophilic allylation; aldehyde; aldimine; ASYMMETRIC ALLYLIC ALKYLATION; DONOR-ACCEPTOR CYCLOPROPANES; COUPLING REACTION; 2-TETRAHYDROPYRANYL ETHERS; AMPHIPHILIC ALLYLATION; ALIPHATIC-ALDEHYDES; BOND-CLEAVAGE; C-ALLYLATION; ALCOHOLS; AMINES;
D O I：
10.1055/s-0034-1378566
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A palladium-catalyzed nucleophilic allylation of aldehydes with vinylcyclopropane in the presence of diethylzinc proceeded to provide homoallyl alcohols with anti stereoselectivity. Aldimines prepared from aldehyde and primary amines in situ underwent a similar nucleophilic allylation to give homoallylamines with syn stereoselectivity. The resulting homoallyl alcohols and homoallylamines could be converted by treatment with a tetranuclear zinc cluster into gamma-vinyl-delta-valerolactones and gamma-vinyl-delta-valerolactams, respectively.
引用
收藏
页码：2306 / 2310
页数：5
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