Rhodium-catalyzed asymmetric nitroallylation of arylmetallics with cyclic nitroallyl acetates and applications in organic synthesis
文献类型：期刊论文
| 作者 | Dong, Lin; Xu, Yan-Jun; Yuan, Wei-Cheng; Cui, Xin; Cun, Lin-Feng; Gong, Liu-Zhu |
| 刊名 | European journal of organic chemistry
 |
| 出版日期 | 2006-09-11 |
| 期号 | 18页码:4093-4105 |
| 关键词 | Asymmetric catalysis Nitroallylation Rhodium complexes (+)-beta-lycorane (+)-gamma-lycorane Chiral nitroalkenes |
| ISSN号 | 1434-193X |
| DOI | 10.1002/ejoc.200600275 |
| 通讯作者 | Dong, lin() |
| 英文摘要 | Highly enantioselective rhodium-catalyzed nitroallylations of arylboronic acids and arylzinc chlorides with cyclic nitroallyl acetates are described. catalyst screening indicated that the rhodium complex of [rh(oh)(cod)](2) and optically pure binap is the optimal catalyst for the nitroallylation of arylboronic acids with 2-nitrocyclohex-2-enyl esters, providing good yields and high enantioselectivities of up to 99% ee. the rhodium complex prepared from rh(acac)(c2h4)(2) and (r)-binap efficiently catalyzed the nitroallylation of arylzinc chlorides with 2-nitrocyclohex-2-enyl acetate at 0 degrees c in high yields of up to 93% and with high enantioselectivities of up to 96% ee. a number of synthetically useful intermediates with high optical purity were prepared with this reaction as starting point: concise total syntheses of optically pure (+)-beta-lycorane in 53% overall yield and of (+)-gamma-lycorane in 52% overall yield were achieved by commencing with the asymmetric nitroallylation of 3,4-methylenedioxyphenylzinc chloride with 2-nitrocyclohex-2-enyl acetate. ((c) wiley-vch verlag gmbh & co. kgaa, 69451 weinheim, germany, 2006). |
| WOS关键词 | 5-ENDO-TRIG RADICAL CYCLIZATION ; ALPHA-HALO AMIDES ; GAMMA-LYCORANE ; CONJUGATE ADDITION ; FORMAL SYNTHESIS ; ORGANOBORONIC ACIDS ; OXABICYCLIC ALKENES ; ALKALOID SYNTHESIS ; ARYLBORONIC ACIDS ; (+/-)-GAMMA-LYCORANE |
| WOS研究方向 | Chemistry |
| WOS类目 | Chemistry, Organic |
| 语种 | 英语 |
| WOS记录号 | WOS:000240662900004 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| URI标识 | http://www.irgrid.ac.cn/handle/1471x/2378726 |
| 专题 | 中国科学院大学 |
| 通讯作者 | Dong, Lin |
| 作者单位 | 1.Chinese Acad Sci, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China 2.Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Peoples R China 3.Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China 4.Chinese Acad Sci, Grad Sch, Beijing, Peoples R China |
| 推荐引用方式 GB/T 7714 | Dong, Lin,Xu, Yan-Jun,Yuan, Wei-Cheng,et al. Rhodium-catalyzed asymmetric nitroallylation of arylmetallics with cyclic nitroallyl acetates and applications in organic synthesis[J]. European journal of organic chemistry,2006(18):4093-4105. |
| APA | Dong, Lin,Xu, Yan-Jun,Yuan, Wei-Cheng,Cui, Xin,Cun, Lin-Feng,&Gong, Liu-Zhu.(2006).Rhodium-catalyzed asymmetric nitroallylation of arylmetallics with cyclic nitroallyl acetates and applications in organic synthesis.European journal of organic chemistry(18),4093-4105. |
| MLA | Dong, Lin,et al."Rhodium-catalyzed asymmetric nitroallylation of arylmetallics with cyclic nitroallyl acetates and applications in organic synthesis".European journal of organic chemistry .18(2006):4093-4105. |
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来源：中国科学院大学
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