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DOI | 10.1126/science.aal5175 |
Formation of alpha-chiral centers by asymmetric beta-C(sp(3))-H arylation, alkenylation, and alkynylation | |
Wu, Qing-Feng1; Shen, Peng-Xiang1; He, Jian1; Wang, Xiao-Bing1; Zhang, Forrest1; Shao, Qian1; Zhu, Ru-Yi1; Mapelli, Claudio2; Qiao, Jennifer X.2; Poss, Michael A.2; Yu, Jin-Quan1 | |
2017-02-03 | |
发表期刊 | SCIENCE |
ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2017 |
卷号 | 355期号:6324页码:499-+ |
文章类型 | Article |
语种 | 英语 |
国家 | USA |
英文摘要 | The enzymatic beta-C-H hydroxylation of the feedstock chemical isobutyric acid has enabled the asymmetric synthesis of a wide variety of polyketides. The analogous transition metal-catalyzed enantioselective beta-C-H functionalization of isobutyric acid-derived substrates should provide a versatile method for constructing useful building blocks with enantioenriched a-chiral centers from this abundant C-4 skeleton. However, the desymmetrization of ubiquitous isopropyl moieties by organometallic catalysts has remained an unanswered challenge. Herein, we report the design of chiral mono-protected aminomethyl oxazoline ligands that enable desymmetrization of isopropyl groups via palladium insertion into the C(sp(3))-H bonds of one of the prochiral methyl groups. We detail the enantioselective beta-arylation, -alkenylation, and -alkynylation of isobutyric acid/2-aminoisobutyric acid derivatives, which may serve as a platform for the construction of a-chiral centers. |
领域 | 地球科学 ; 气候变化 ; 资源环境 |
收录类别 | SCI-E |
WOS记录号 | WOS:000393183100039 |
WOS关键词 | C-H ARYLATION ; BETA-HYDROXYISOBUTYRIC ACID ; BOND ACTIVATION ; C(SP(3))-H BONDS ; ISOBUTYRIC ACID ; MILD CONDITIONS ; LIGAND ; FUNCTIONALIZATION ; AUXILIARY ; INDOLINES |
WOS类目 | Multidisciplinary Sciences |
WOS研究方向 | Science & Technology - Other Topics |
URL | 查看原文 |
引用统计 | |
文献类型 | 期刊论文 |
条目标识符 | http://119.78.100.173/C666/handle/2XK7JSWQ/195342 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | 1.Scripps Res Inst, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA; 2.Bristol Myers Squibb Co, Discovery Chem Res & Dev, POB 4000, Princeton, NJ 08543 USA |
推荐引用方式 GB/T 7714 | Wu, Qing-Feng,Shen, Peng-Xiang,He, Jian,et al. Formation of alpha-chiral centers by asymmetric beta-C(sp(3))-H arylation, alkenylation, and alkynylation[J]. SCIENCE,2017,355(6324):499-+. |
APA | Wu, Qing-Feng.,Shen, Peng-Xiang.,He, Jian.,Wang, Xiao-Bing.,Zhang, Forrest.,...&Yu, Jin-Quan.(2017).Formation of alpha-chiral centers by asymmetric beta-C(sp(3))-H arylation, alkenylation, and alkynylation.SCIENCE,355(6324),499-+. |
MLA | Wu, Qing-Feng,et al."Formation of alpha-chiral centers by asymmetric beta-C(sp(3))-H arylation, alkenylation, and alkynylation".SCIENCE 355.6324(2017):499-+. |
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