Ruthenium(II) porphyrin catalyzed cyclopropanation of alkenes with tosylhydrazones

被引：65
|
作者：
Zhang, JL
Chan, PWH
Che, CM
机构：
[1] Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China
[2] Univ Hong Kong, Open Lab Chem Biol, Inst Mol Technol Drug Discovery & Synth, Hong Kong, Hong Kong, Peoples R China
来源：
TETRAHEDRON LETTERS | 2003年 / 44卷 / 48期
关键词：
D O I：
10.1016/j.tetlet.2003.09.157
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The diastereoselective ruthenium(II) porphyrin catalyzed cyclopropanation of a variety of alkenes with aryl diazomethanes generated in situ from stable tosylhydrazone derivatives, was achieved in good to excellent yields (up to 92%) and product turnovers. The practical utility of [Ru-II(p-Cl-TPP)(CO)] (H-2(p-Cl-TPP) = meso-tetrakis(p-chlorophenyl)porphyrin) 3 was illustrated in the synthesis of the potent HIV-1 reverse transcriptase inhibitor 10. Preferential formation of sulfone products for reactions involving o- and m-monosubstituted aryl tosylhydrazones demonstrated a hitherto unknown ruthenium(11) porphyrin catalyzed sulfonation reaction. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码：8733 / 8737
页数：5
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