Asymmetric friedel-crafts alkylation of methoxyfuran with nitroalkenes catalyzed by diphenylamine-tethered Bis(oxazoline)-Zn(II) complexes

被引：79
作者：
Liu, Han [1 ]
Xu, Jiaxi [1 ]
Du, Da-Ming [1 ]
机构：
[1] Peking Univ, BNLMS, Key Lab Bioorgan Chem & Mol Engn, Minist Educ,Coll Chem & Mol Engn, Beijing 100871, Peoples R China
来源：
ORGANIC LETTERS | 2007年 / 9卷 / 23期
关键词：
D O I：
10.1021/ol702003x
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first catalytic asymmetric Friedel-Crafts reaction of 2-methoxyfuran with nitroalkenes was developed under the catalysis of diphenylamine-tethered bis(oxazoline)-Zn(OTf)(2) complexes. The reaction conditions and ligands were optimized, and the scope of the reaction was tested by varying the nitroalkenes. For most of aromatic and heteroaromatic nitroalkenes, good yields and high enantioselectivities (86-96% ee) were obtained, The methoxyfuran group in the product can be transformed to carboxylic acid via oxidative fragmentation with full retention of the configuration.
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页码：4725 / 4728
页数：4
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