Journal ArticleDOI
Substrate-Controlled Domino Reactions of Crotonate-Derived Sulfur Ylides: Synthesis of Benzothiophene Derivatives.
Reads0
Chats0
TLDR
In these reactions, crotonate-derived sulfur ylides acting as two-carbon synthons in annulation reactions are reported for the first time and reaction mechanisms for these domino reactions are proposed, one of which is supported by DFT calculations.Abstract:
Substrate-controlled domino reactions between thioaurones or their analogues and crotonate-derived sulfur ylides were developed and produced a broad spectrum of benzothiophene-fused pyran derivatives, substituted chromene derivatives. In these reactions, crotonate-derived sulfur ylides acting as two-carbon synthons (α and β carbons or β and γ carbons) in annulation reactions are reported for the first time. These investigations nicely complement and expand previously studied reactions of crotonate-derived sulfur ylides. In addition, reaction mechanisms for these domino reactions are proposed, one of which is supported by DFT calculations.read more
Citations
More filters
Journal ArticleDOI
C-H Methylation of Iminoamido Heterocycles with Sulfur Ylides*
Prithwish Ghosh,Na Yeon Kwon,Saegun Kim,Sangil Han,Suk Hun Lee,Won An,Neeraj Kumar Mishra,Soo Bong Han,In Su Kim +8 more
TL;DR: The unprecedented C(sp 2 )-H methylation of iminoamido heterocycles as nucleoside base analogues is described, which can be readily applied to the site-selectivemethylation of azauracil nucleosides.
Journal ArticleDOI
Synthesis of Bicyclo[4.1.0]tetrahydropyridazines by a Sequential [4 + 2] and [1 + 2] Annulation Reaction of Azoalkenes and Crotonate-Derived Sulfur Ylides.
TL;DR: This protocol provides a novel and practical method for the synthesis of cyclopropane-fused tetrahydropyridazines with a quaternary carbon center in synthetically useful yield.
Journal ArticleDOI
Recent Advances in the Cycloaddition Reactions of 2‐Benzylidene‐1‐benzofuran‐3‐ones, and Their Sulfur, Nitrogen and Methylene Analogues
Qingsong Deng,Xiangtai Meng +1 more
TL;DR: In this review, the derivatives of four structures synthesized from 2-benzylidene-1-benZofuran-3-one and their analogues are classified in terms of their ring size and type, as well as summarizing the developments of this field.
Journal ArticleDOI
Construction of Eight-Membered Cyclic Diaryl Sulfides via Domino Reaction of Arynes with Thioaurone Analogues and DFT Study on the Reaction Mechanism.
TL;DR: Density functional theory calculations were performed to elucidate the reaction mechanism, which involves the elementary steps of the [3 + 2] cycloaddition, 1,2-hydrogen shift, and C(sp2)-S bond cleavage as well as the substituent effect.
Journal ArticleDOI
Construction of benzothiophene fused pyrrolidone in water via a catalyst-free process and a mechanism study
TL;DR: In this paper, a three-component domino reaction towards benzothiophene fused pyrrolidone derivatives was developed in an environmentally benign manner, and the reaction proceeded well in aqueous media, and delivered the desired products in high yields with excellent selectivity.
References
More filters
Journal ArticleDOI
Ylide-initiated michael addition-cyclization reactions beyond cyclopropanes.
Xiu-Li Sun,Yong Tang +1 more
TL;DR: This Account outlines the recent work on ylide-initiated Michael addition/cyclization reactions by altering the heteroatoms and the ligands of the ylides, which provide easy access to diverse cyclic compounds with the ability to control regioselectivity, chemoselectiveness, diastereoselectivities, and enantioselectedivity.
Journal ArticleDOI
Enantioselective synthesis of vinylcyclopropanes and vinylepoxides mediated by camphor-derived sulfur ylides: rationale of enantioselectivity, scope, and limitation.
Xianming Deng,Ping Cai,Song Ye,Xiu-Li Sun,Wei-Wei Liao,Kai Li,Yong Tang,Yun-Dong Wu,Li-Xin Dai +8 more
TL;DR: By a sidearm approach, camphor-derived sulfur ylides 1 were designed and synthesized for the cyclopropanation of electron-deficient alkenes and epoxidation of aldehydes and the sidearmed hydroxyl group was found to play a key role in the control of enantioselectivity and diastereoselectivities.
Journal ArticleDOI
A novel chiral sulfonium yilde: highly enantioselective synthesis of vinylcyclopropanes.
TL;DR: A newly designed chiral sulfonium allylide reacted with alpha,beta-unsaturated esters, ketones, amides, and nitriles to afford trans-2-silylvinyl-trans-3-substituted cyclopropyl esters and excellent enantioselectivity in good to high yields.
Journal ArticleDOI
[3 + 1]- and [3 + 2]-Cycloadditions of Azaoxyallyl Cations and Sulfur Ylides.
TL;DR: A new formal [3 + 1]-cycloaddition reaction of azaoxyallyl cation intermediates, generated in situ from α-halo hydroxamates bearing α-alkyl groups, and sulfur ylides is reported, furnishing useful β-lactams in fair to modest yields.
Journal ArticleDOI
On the Mechanism of Ylide-Mediated Cyclopropanations: Evidence for a Proton-Transfer Step and Its Effect on Stereoselectivity
Samantha L. Riches,Chandreyee Saha,Noelia Fontán Filgueira,Emma Grange,Eoghan M. McGarrigle,Varinder K. Aggarwal +5 more
TL;DR: By applying this model to S-, N-, and P-ylides the authors have been able to rationalize the outcome of different ylide reactions bearing a variety of substituents in terms of chemo- and enantioselectivity.