GSTDTAP  > 地球科学
DOI10.1126/science.aaq0445
Activation of olefins via asymmetric Bronsted acid catalysis
Tsuji, Nobuya1; Kennemur, Jennifer L.1; Buyck, Thomas1; Lee, Sunggi1; Prevost, Sebastien1; Kaib, Philip S. J.1; Bykov, Dmytro2,3; Fares, Christophe1; List, Benjamin1
2018-03-30
发表期刊SCIENCE
ISSN0036-8075
EISSN1095-9203
出版年2018
卷号359期号:6383页码:1501-+
文章类型Article
语种英语
国家Germany; USA
英文摘要

The activation of olefins for asymmetric chemical synthesis traditionally relies on transition metal catalysts. In contrast, biological enzymes with Bronsted acidic sites of appropriate strength can protonate olefins and thereby generate carbocations that ultimately react to form natural products. Although chemists have recently designed chiral Bronsted acid catalysts to activate imines and carbonyl compounds, mimicking these enzymes to protonate simple olefins that then engage in asymmetric catalytic reactions has remained a substantial synthetic challenge. Here, we show that a class of confined and strong chiral Bronsted acids enables the catalytic asymmetric intramolecular hydroalkoxylation of unbiased olefins. The methodology gives rapid access to biologically active 1,1-disubstituted tetrahydrofurans, including (-)-Boivinianin A.


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:000428657000040
WOS关键词ANTI-MARKOVNIKOV HYDROETHERIFICATION ; NONACTIVATED ALKENES ; METAL CATALYSIS ; TRIFLIC ACID ; HYDROALKOXYLATION ; ENANTIOSELECTIVITY ; FUNCTIONALIZATION ; HYDROAMINATION ; ALDEHYDES ; DIENES
WOS类目Multidisciplinary Sciences
WOS研究方向Science & Technology - Other Topics
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文献类型期刊论文
条目标识符http://119.78.100.173/C666/handle/2XK7JSWQ/198297
专题地球科学
资源环境科学
气候变化
作者单位1.Max Planck Inst Kohlenforsch, Kaiser Wilhelm Pl 1, D-45470 Mulheim, Germany;
2.Oak Ridge Natl Lab, Natl Ctr Computat Sci, Oak Ridge, TN 37831 USA;
3.Max Planck Inst Chem Energy Convers, Stiftstr 34-36, D-45470 Mulheim, Germany
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GB/T 7714
Tsuji, Nobuya,Kennemur, Jennifer L.,Buyck, Thomas,et al. Activation of olefins via asymmetric Bronsted acid catalysis[J]. SCIENCE,2018,359(6383):1501-+.
APA Tsuji, Nobuya.,Kennemur, Jennifer L..,Buyck, Thomas.,Lee, Sunggi.,Prevost, Sebastien.,...&List, Benjamin.(2018).Activation of olefins via asymmetric Bronsted acid catalysis.SCIENCE,359(6383),1501-+.
MLA Tsuji, Nobuya,et al."Activation of olefins via asymmetric Bronsted acid catalysis".SCIENCE 359.6383(2018):1501-+.
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