Open AccessDOI
N-Sulfanylimides as the Sulfur Source for Alkyl Allenyl Sulfoxides via [2,3]-Sigmatropic Rearrangement
Adam B. Riddell,Michelle M. Michalski,Monika R. Snowdon,Mark J. Hirst,Adrian L. Schwan +4 more
- Vol. 6, Iss: 41, pp 11331-11336
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The article was published on 2021-11-08 and is currently open access. It has received 2 citations till now. The article focuses on the topics: Sigmatropic reaction & 2,3-sigmatropic rearrangement.read more
Citations
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Journal ArticleDOI
One-pot thiol-free synthetic approach to sulfides, and sulfoxides selectively
TL;DR: In this article , a facile and efficient thiol-free one-pot method for direct synthesis of sulfides and sulfoxides under green conditions without using any metal catalyst is reported.
Journal ArticleDOI
Synthesis of alkyl allenyl sulfoxides from thiosuccinimides via [2,3]-sigmatropic rearrangement
TL;DR: In this article , a variety of alkyl allenyl sulfoxides were synthesized in fair to good yields (21−73%, 21 examples) with the optimized conditions of excess propargyl alcohol and potassium carbonate in chloroform at 50°C.
References
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Journal ArticleDOI
Prepackaged Ramberg–Bäcklund reagents: useful tools for organic synthesis
TL;DR: In this article, the synthesis and reactions of α,β-unsaturated chloromethyl sulfones are presented, which serve as prepackaged Ramberg-Backlund reagents, which following an appropriate first step such as Diels-Alder addition, react with base giving Ramberg−Backlund products.
Journal ArticleDOI
Rhodium(I)‐Catalyzed Cycloisomerization of Allene–Allenylcyclopropanes
TL;DR: The first cycloisomerization of allene-allenylcyclopropanes was described in this article, where ethylene was liberated from the cyclopropane ring to afford the 1,5,6,7-tetrahydroazulene skeletons.
Journal ArticleDOI
Divergent Synthesis of Trifluoromethyl Sulfoxides and β-SCF3 Carbonyl Compounds by Tandem Trifluoromethylthiolation/Rearrangement of Allylic and Propargylic Alcohols.
TL;DR: A selenium-catalyzed trifluoromethylthiolation/[2,3]-sigmatropic rearrangement of tertiary allylic and propargylic alcohols which could provide straightforward and facile access to trif Klu Klux Klan sulfoxides was developed.
Journal ArticleDOI
Organocatalytic Asymmetric α-Sulfenylation of 2-Substituted Indolin-3-ones: A Strategy for the Synthesis of Chiral 2,2-Disubstituted Indole-3-ones with S- and N-Containing Heteroquaternary Carbon Stereocenter
Yong-Long Zhao,Xing-Hai Fei,Yong-Qin Tang,Peng-Fei Xu,Fen-Fen Yang,Bin He,Xiao-Zhong Fu,Yuan-Yong Yang,Meng Zhou,Yuanhu Mao,Yong-Xi Dong,Chun Li +11 more
TL;DR: An organocatalytic asymmetric α-sulfenylation of 2-substituted indolin-3-ones with N-(alkylthio or arylthio)succinimides has been developed for the first time using Cinchona-derived squaramide as the catalyst.
Journal ArticleDOI
Cleavage of oxygen–sulfur double bonds and carbon–sulfur bonds: unusual highly selective electrophilic addition of allenylic sulfoxides
TL;DR: It is reported that hydrogen bonding may mediate efficient and highly selective cleavage of OS and C–S bonds in 1,2-allenyl sulfoxides with I2 and BnSH, which transfer the oxygen to the adjacent allenylic carbon atom forming a ketone or aldehyde carbonyl functionality with one CC bond in the allene moiety remaining in a highly stereoselective manner.
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