Highly Efficient Asymmetric Synthesis of Vinylic Amino Alcohols by Zn-Promoted Benzoyloxyallylation of Chiral N-tert-Butanesulfinyl Imines: Facile and Rapid Access to (-)-Cytoxazone
文献类型：期刊论文
| 作者 | Liu, Min2; Sun, Xing-Wen2; Xu, Ming-Hua1,2 ; Lin, Guo-Qiang2
|
| 刊名 | CHEMISTRY-A EUROPEAN JOURNAL
 |
| 出版日期 | 2009 |
| 卷号 | 15期号:39页码:10217-10224 |
| 关键词 | amino alcohols asymmetric synthesis chiral auxiliaries (-)-cytoxazone hydroxyallylation |
| ISSN号 | 0947-6539 |
| DOI | 10.1002/chem.200900801 |
| 文献子类 | Article |
| 英文摘要 | All efficient and convenient alpha-hydroxyallylation approach for the asymmetric synthesis of a variety of beta-amino-alpha-vinyl alcohols has been successfully developed A wide range of vinylic amino alcohol derivatives could be obtained in very rood yields and with excellent diastereomeric ratios of up to 991 in favor of anti isomers by highly diastereoselective Zn-promoted benzoyloxyallylation of chiral N-tert-butanesulfinyl imines with 3-bromopropenyl benzoate. at room temperature. Ill particular. excellent enantioinduction of the two new stereogenic centers was observed. with up to 98% cc The method provides it new route for the direct alpha-hydroxyallylation of imines ill a highly stereoselective manner. Moreover, the synthetic value of the Method has also been demonstrated by the most concise and straightforward synthesis of (-)-cytoxazone yet reported |
| WOS关键词 | ANTI-BETA-AMINO ; RING-OPENING REACTIONS ; MANNICH-TYPE REACTION ; TAXOL SIDE-CHAIN ; STEREOSELECTIVE-SYNTHESIS ; 1,2-AMINO ALCOHOLS ; ENANTIOSELECTIVE SYNTHESIS ; CHLOROSULFONYL ISOCYANATE ; ORGANIC-SYNTHESIS ; DIASTEREOSELECTIVE SYNTHESIS |
| 资助项目 | National Natural Science Foundation of China[20672123] ; National Natural Science Foundation of China[20672126] ; National Natural Science Foundation of China[20721003] ; National Natural Science Foundation of China[20772017] ; Chinese Academy of Sciences[00000000] ; Shanghai Rising-Star Program[08QH14027] ; Major State Basic Research Development Program[2006CB06106] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000270854200032 |
| 出版者 | WILEY-BLACKWELL |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/279354]  |
| 专题 | 药物化学研究室 |
| 通讯作者 | Xu, Ming-Hua |
| 作者单位 | 1.Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China 2.Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China; |
| 推荐引用方式 GB/T 7714 | Liu, Min,Sun, Xing-Wen,Xu, Ming-Hua,et al. Highly Efficient Asymmetric Synthesis of Vinylic Amino Alcohols by Zn-Promoted Benzoyloxyallylation of Chiral N-tert-Butanesulfinyl Imines: Facile and Rapid Access to (-)-Cytoxazone[J]. CHEMISTRY-A EUROPEAN JOURNAL,2009,15(39):10217-10224. |
| APA | Liu, Min,Sun, Xing-Wen,Xu, Ming-Hua,&Lin, Guo-Qiang.(2009).Highly Efficient Asymmetric Synthesis of Vinylic Amino Alcohols by Zn-Promoted Benzoyloxyallylation of Chiral N-tert-Butanesulfinyl Imines: Facile and Rapid Access to (-)-Cytoxazone.CHEMISTRY-A EUROPEAN JOURNAL,15(39),10217-10224. |
| MLA | Liu, Min,et al."Highly Efficient Asymmetric Synthesis of Vinylic Amino Alcohols by Zn-Promoted Benzoyloxyallylation of Chiral N-tert-Butanesulfinyl Imines: Facile and Rapid Access to (-)-Cytoxazone".CHEMISTRY-A EUROPEAN JOURNAL 15.39(2009):10217-10224. |
入库方式： OAI收割
来源：上海药物研究所
浏览0
下载0
收藏0
其他版本
除非特别说明，本系统中所有内容都受版权保护，并保留所有权利。