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Highly Regio- and Enantioselective Alkoxycarbonylative Amination of Terminal Allenes Catalyzed by a Spiroketal-Based Diphosphine/Pd(II) Complex
Alternative Title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
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
2015
Source PublicationJ. Am. Chem. Soc.
Volume137Issue:49Pages:15346-15349
AbstractAn 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.
Subtype论文
Subject Area金属有机化学
DOI10.1021/jacs.5b07764
URL查看原文
Indexed BySCI
Language英语
WOS IDWOS:000366874700003
Citation statistics
Cited Times:31[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/39679
Collection金属有机化学国家重点实验室
Corresponding AuthorWang Z(王正); Ding KL(丁奎岭)
Affiliation1.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
Recommended Citation
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.
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