Copper(I)‐Catalyzed (<i>Z</i>)‐β‐(Tosyloxy)alkenyl Iodide Synthesis from (Aryl)[(<i>E</i>)‐β‐(tosyloxy)alkenyl]iodonium Tosylates: Diversity‐Oriented Synthesis of Trisubstituted Alkenes

Mondal, Keshab Chandra; Pan, Subhas Chandra

doi:10.1002/ejoc.201500039

Cited by 14 publications

(7 citation statements)

References 51 publications

(10 reference statements)

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“…This was achieved by Sonogashira and reduction reactions without any loss of stereoselectivity or reduction in the deuterium ratio, further demonstrating the potential of cis ‐ β ‐phenol‐VBX derivatives as phenol‐derived building blocks (Scheme 6 and 7). [16k] …”

Section: Methodsmentioning

confidence: 99%

Synthesis of Phenol‐Derived cis‐Vinyl Ethers Using Ethynyl Benziodoxolone

Ura

Shimbo

Yudasaka

et al. 2020

Chemistry An Asian Journal

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The stereoselective synthesis of cis-β-phenoxyvinyl benziodoxolones (cis-β-phenol-VBXs) from an ethynyl benziodoxolone-acetonitrile complex (EBX-MeCN) and various phenols is reported herein. The reaction tolerates different phenol derivatives, including complex natural products, and can be conducted under mild conditions. The synthesis was performed in an aqueous solvent in the absence and presence of a catalytic amount of a base. Selectively mono-and di-deuterated cis-β-phenol-VBXs were also prepared. cis-β-Phenol-VBXs were stereospecifically derivatized to cis-alkynylvinyl ethers and cis-iodovinyl ethers without loss of stereoselectivity or reduction in the deuterium/hydrogen ratio.

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Section: Methodsmentioning

confidence: 99%

Synthesis of Phenol‐Derived cis‐Vinyl Ethers Using Ethynyl Benziodoxolone

Ura

Shimbo

Yudasaka

et al. 2020

Chemistry An Asian Journal

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“…An analogous approach to the synthesis of trisubstituted alkenes was reported by Pan, 17 who performed the copper(I)-catalyzed synthesis of (Z)--(tosyloxy)alkenyl iodides S6-1 (Scheme S6). The same group also demonstrated the ability of (Z)--(tosyloxy)alkenyl iodides to undergo the gradual replacement of the iodine and, subsequently, the tosyloxy group.…”

Section: Scheme S4 Stereoselective Synthesis Of Terminal Vinyl Monoflmentioning

confidence: 99%

Cross-Coupling Reactions of Double or Triple Electrophilic Templates for Alkene Synthesis

Edlová¹,

Čubiňák²,

Tobrman³

2020

Synthesis

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This short review summarizes the latest advances in the cross-coupling reactions of double and triple electrophilic templates bearing halogen atoms and an activated C–O bond. Reactions involving the formation of a C–C bond as part of di-, tri-, and tetrasubstituted double bond systems are highlighted.1 Introduction2 Cross-Coupling Reactions of Halovinyl Tosylates3 Cross-Coupling Reactions of Halovinyl Triflates4 Cross-Coupling Reactions of Halovinyl Phosphates5 Cross-Coupling Reactions of Halovinyl Esters6 Conclusion

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“…The Cu-catalysed azide-alkyne cycloaddition (CuAAC) reaction constitutes one of the most interesting examples of the click reaction (Bae et al, 2005;Cheng et al, 2012;Mondal & Pan, 2015). Trisubstituted alkenes are commonly found in the molecular skeleton of natural products and bioactive substances, and they are important building blocks in organic chemistry (Zhu et al, 2012;Manikandan & Jeganmohan, 2015).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structures of (E)-3-(furan-2-yl)-2-phenyl-N-tosylacrylamide and (E)-3-phenyl-2-(m-tolyl)-N-tosylacrylamide

et al. 2016

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In the title N-tosylacrylamide compounds, (I) and (II), the conformation about the C=C bond is E. In (I), the furan, phenyl and 4-methylbenzene rings are inclined to the acrylamide mean plane [–NH—C(= O)—C=C–] by 26.47 (11), 69.01 (8) and 82.49 (9)°, respectively. In (II), the phenyl, and 3-methyl and 4-methylbenzene rings are inclined to the acrylamide mean plane by 11.61 (10), 78.44 (10) and 78.24 (10)°, respectively. In the crystals of both compounds, molecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers with (8) ring motifs.

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Copper(I)‐Catalyzed (Z)‐β‐(Tosyloxy)alkenyl Iodide Synthesis from (Aryl)[(E)‐β‐(tosyloxy)alkenyl]iodonium Tosylates: Diversity‐Oriented Synthesis of Trisubstituted Alkenes

Abstract: The treatment of iodonium tosylates (I) with a catalytic amount of CuCl leads to desired (Z)‐β‐(tosyloxy)alkenyl iodides (II), which are converted into tamoxifen intermediate (IV) and other trisubstituted alkenes (VII) and (X).

Cited by 14 publications

References 51 publications

Synthesis of Phenol‐Derived cis‐Vinyl Ethers Using Ethynyl Benziodoxolone

Synthesis of Phenol‐Derived cis‐Vinyl Ethers Using Ethynyl Benziodoxolone

Cross-Coupling Reactions of Double or Triple Electrophilic Templates for Alkene Synthesis

Crystal structures of (E)-3-(furan-2-yl)-2-phenyl-N-tosylacrylamide and (E)-3-phenyl-2-(m-tolyl)-N-tosylacrylamide

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