Styrylmalonates as an Alternative to Donor-Acceptor Cyclopropanes in the Reactions with Aldehydes: A Route to 5,6-Dihydropyran-2-ones

被引：29
|
作者：
Borisov, Denis D. [1 ]
Novikov, Roman A. [1 ,2 ]
Eltysheva, Anna S. [1 ]
Tkachev, Yaroslav V. [2 ]
Tomiloy, Yury V. [1 ]
机构：
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Prosp, Moscow 119991, Russia
[2] Russian Acad Sci, Engelhardt Inst Mol Biol, 32 Vavilov St, Moscow 119991, Russia
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 14期
基金：
俄罗斯科学基金会;
关键词：
AROMATIC-ALDEHYDES; DERIVATIVES; CYCLOADDITION; NITROSOARENES; CONSTRUCTION; ANNULATION; MECHANISM;
D O I：
10.1021/acs.orglett.7b01556
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new strategy for modifying the reactivity of donor-acceptor cyclopropanes (DAC) has been suggested. It involves the use of isomeric styrylmalonates as alternative sources of reactive intermediates. The efficiency of the approach has been demonstrated in reactions with aromatic aldehydes. As a result, a new process for Construction of the 5,6-dihydropyran-2-one skeleton has been developed. It efficiently occurs with high diastereoselectivity in the presence of BF3.Et(2)Q; the products can be easily isolated by crystallization. The subsequent use of the resulting dihydropyranones in syntheses providing convenient access to various classes of compounds with broad molecular diversity has been demonstrated.
引用
收藏
页码：3731 / 3734
页数：4
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