Highly Regio- and Enantioselective Alkoxycarbonylative Amination of Terminal Allenes Catalyzed by a Spiroketal-Based Diphosphine/Pd(II) Complex
文献类型：期刊论文
| 作者 | Liu JW(刘家旺)1; Han ZB(韩召斌)1; Wang XM(王晓明)1; Wang Z(王正)1; Ding KL(丁奎岭)1 |
| 刊名 | J. Am. Chem. Soc.
 |
| 出版日期 | 2015 |
| 卷号 | 137期号:49页码:15346-15349 |
| 其他题名 | 螺缩酮双膦配体/钯(II)络合物催化的高区域和对映选择性末端联烯烷氧羰化胺化 |
| 通讯作者 | 王正 ; 丁奎岭 |
| 英文摘要 | An enantioselective alkoxycarbonylation-amination cascade process of terminal allenes with CO, methanol, and arylamines has been developed. It proceeds under mild conditions (room temperature, ambient pressure CO) via oxidative Pd(II) catalysis using an aromatic spiroketal-based diphosphine (SKP) as a chiral ligand and a Cu(II) salt as an oxidant and affords a wide range of alpha-methylene-beta-arylamino acid esters (36 examples) in good yields with excellent enantioselectivity (up to 96% ee) and high regioselectivity (branched/linear > 92:8). Preliminary mechanistic studies suggested that the reaction is likely to proceed through alkoxycarbonylpalladation of the allene followed by an amination process. The synthetic utility of the protocol is showcased in the asymmetric construction of a cydoheptene-fused chiral beta-lactam. |
| 学科主题 | 金属有机化学 |
| 收录类别 | SCI |
| 原文出处 | http://dx.doi.org/10.1021/jacs.5b07764 |
| 语种 | 英语 |
| WOS记录号 | WOS:000366874700003 |
| 源URL | [http://ir.sioc.ac.cn/handle/331003/39679]  |
| 专题 | 上海有机化学研究所_金属有机化学国家重点实验室 |
| 作者单位 | 1.中科院上海有机化学研究所, 金属有机化学国家重点实验室 2.天津化学化工协同创新中心 |
| 推荐引用方式 GB/T 7714 | Liu JW,Han ZB,Wang XM,et al. Highly Regio- and Enantioselective Alkoxycarbonylative Amination of Terminal Allenes Catalyzed by a Spiroketal-Based Diphosphine/Pd(II) Complex[J]. J. Am. Chem. Soc.,2015,137(49):15346-15349. |
| APA | 刘家旺,韩召斌,王晓明,王正,&丁奎岭.(2015).Highly Regio- and Enantioselective Alkoxycarbonylative Amination of Terminal Allenes Catalyzed by a Spiroketal-Based Diphosphine/Pd(II) Complex.J. Am. Chem. Soc.,137(49),15346-15349. |
| MLA | 刘家旺,et al."Highly Regio- and Enantioselective Alkoxycarbonylative Amination of Terminal Allenes Catalyzed by a Spiroketal-Based Diphosphine/Pd(II) Complex".J. Am. Chem. Soc. 137.49(2015):15346-15349. |
入库方式： OAI收割
来源：上海有机化学研究所
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