- Enantioselective Reductive Divinylation of Unactivated Alkenes by Nickel-Catalyzed Cyclization Coupling Reaction
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Catalytic asymmetric dicarbofunctionalization of tethered alkenes has emerged as a promising tool for producing chiral cyclic molecules; however, it typically relies on aryl-tethered alkenes to form benzene-fused compounds. Herein, we report an enantioselective cross-electrophile divinylation reaction of nonaromatic substrates, 2-bromo-1,6-dienes. The approach thus offers a route to new chiral cyclic architectures, which are key structural motifs found in various biologically active compounds. The reaction proceeds under mild conditions, and the use of chiral t-Bu-pmrox and 3,5-difluoro-pyrox ligands resulted in the formation of divinylated products with high chemo-, regio-, and enantioselectivity. The method is applicable for the incorporation of chiral hetero- and carbocycles into complex molecules.
- Peng, Xuejing,Qiao, Jin-Bao,Shu, Xing-Zhong,Yao, Qi-Wei,Zhang, Ya-Qian,Zhao, Zhen-Zhen
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supporting information
p. 12961 - 12967
(2021/09/03)
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- A Radical-Initiated Fragmentary Rearrangement Cascade of Ene-Ynamides to [1,2]-Annulated Indoles via Site-Selective Cyclization
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Straightforward access to [1,2]-annulated indoles, key substructures in natural products, is highly desirable yet challenging. Herein, a radical triggered fragmentary cyclization cascade reaction of ene-ynamides is presented, providing a rapid access into [1,2]-annulated indoles by an intermolecular radical addition, intramolecular cyclization, desulfonylative aryl migration, and site-selective C(sp2)-N cyclization sequence. DFT calculations support oxidation of N-centered radical species to cations prior to the C-N bond formation, followed by an unusual aza-Nazarov cyclization.
- Li, Sifan,Wang, Yu,Wu, Zibo,Shi, Weiliang,Lei, Yibo,Davies, Paul W.,Shu, Wei
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supporting information
p. 7209 - 7214
(2021/09/14)
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- Reactivity of Arynes for Arene Dearomatization
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An unprecedented aryne-mediated dearomatization reaction is described. An aryne intermediate generated from arenesulfonyl ynamide-tethered triynes and tetraynes reacts with both the π-systems of a tethered alkene and the arenesulfonyl group to generate cy
- Karmakar, Rajdip,Le, Anh,Xie, Peipei,Xia, Yuanzhi,Lee, Daesung
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supporting information
p. 4168 - 4172
(2018/07/29)
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- 15 and 30-Membered polyolefinic macrocycles. Periphery modification by aromatic nucleophilic substitution of fluorine
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Tris[(4-fluorophenyl)sulfonyl]-1,6,11-triazacyclopentadeca-3,8,13-triene is a pivotal 15-membered triolefinic macrocycle from which a vast array of different derivatives are prepared by substitution of fluorine atoms.
- Moreno-Ma?as, Marcial,Spengler, Jan
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p. 7769 - 7774
(2007/10/03)
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