Asymmetric cycloisomerization/[3 + 2] cycloaddition for the synthesis of chiral spiroisobenzofuran-1,3′-pyrrolidine derivatives DOI
Pei Dong, Long Chen, Zhendong Yang

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(24), P. 6874 - 6880

Published: Jan. 1, 2021

An asymmetric tandem cycloisomerization/[3 + 2] cycloaddition reaction of 2,2′-diester aziridine and 2-ethynyl benzyl alcohol with Au( i )/chiral N , ′-dioxide−Dy( iii ) as a relay catalyst system was developed.

Language: Английский

2-Azaallyl Anions, 2-Azaallyl Cations, 2-Azaallyl Radicals, and Azomethine Ylides DOI
Shaojian Tang, Xia Zhang, Jiayue Sun

et al.

Chemical Reviews, Journal Year: 2018, Volume and Issue: 118(20), P. 10393 - 10457

Published: Oct. 10, 2018

This review covers the use of 2-azaallyl anions, cations, and radicals in organic synthesis up through June 2018. Particular attention is paid to both foundational studies recent advances over past decade involving semistabilized nonstabilized anions as key intermediates various carbon–carbon carbon–heteroatom bond-forming processes. Both transition-metal-catalyzed transition-metal-free transformations are covered. Azomethine ylides, which have received significant elsewhere, discussed briefly with primary focus on critical comparisons regard generation use.

Language: Английский

Citations

196
Isocyanide-based multicomponent reactions in the synthesis of heterocycles DOI
Samahe Sadjadi, Majid Μ. Heravi,

Niousha Nazari

et al.

RSC Advances, Journal Year: 2016, Volume and Issue: 6(58), P. 53203 - 53272

Published: Jan. 1, 2016

In this review, we update our previous presentation, underscoring the recent applications of isocyanides as privileged synthons in synthesis various heterocyclic compounds, especially focused on those synthesizedviamulticomponent reactions.

Language: Английский

Citations

161
Recent advances in synthetic facets of immensely reactive azetidines DOI Creative Commons

Vishu Mehra,

Isha Lumb,

Amit Ȧnand

et al.

RSC Advances, Journal Year: 2017, Volume and Issue: 7(72), P. 45763 - 45783

Published: Jan. 1, 2017

Recent developments in synthetic strategies towards functionalized azetidines along with their versatility as heterocyclic synthons.

Language: Английский

Citations

89
Asymmetric synthesis of tetrazole and dihydroisoquinoline derivatives by isocyanide-based multicomponent reactions DOI Creative Commons
Qian Xiong, Shunxi Dong, Yushuang Chen

et al.

Nature Communications, Journal Year: 2019, Volume and Issue: 10(1)

Published: May 9, 2019

Abstract Although isocyanide-based multicomponent reactions were proven to be simple, elegant and facile strategies for the synthesis of highly valuable nitrogen-containing heterocycles, their asymmetric versions accessing optically active nitrogen heterocyclic compounds are rather limited. Here, we illustrate that, relying on enantioselective addition simple isocyanides C=C bonds, several realized in presence a chiral Mg II - N , ʹ-dioxide catalyst. In reaction among isocyanide, TMSN 3 alkylidene malonate, three- or four-component could precisely controlled by modulating conditions, supplying two types enantioenriched tetrazole-derivatives moderate high yields. Possible catalytic cycles via key zwitterionic intermediate, vital roles H 2 O excess ligand provided based control experiments. Moreover, taking advantage this intermediate as 1,3-dipole, an dearomative [3+2] annulation nonactivated isoquinolines is achieved, furnishing 1,2-dihydroisoquinolines good excellent results.

Language: Английский

Citations

72
Asymmetric [3 + 2] cycloaddition of donor–acceptor aziridines with aldehydes via carbon–carbon bond cleavage DOI Creative Commons
Yuting Liao, Xiaohua Liu, Yu Zhang

et al.

Chemical Science, Journal Year: 2016, Volume and Issue: 7(6), P. 3775 - 3779

Published: Jan. 1, 2016

An enantioselective [3 + 2] annulation of donor–acceptor aziridines with aldehydes utilizing a relay catalyst system Nd(OTf)3/N,N′-dioxide/LiNTf2 has been realized.

Language: Английский

Citations

48
Advances in synthesis and chemistry of aziridines DOI
Girija S. Singh

Advances in heterocyclic chemistry, Journal Year: 2019, Volume and Issue: unknown, P. 245 - 335

Published: Jan. 1, 2019

Language: Английский

Citations

45
Ring Expansions of Activated Aziridines and Azetidines DOI
Manas K. Ghorai, Aditya Bhattacharyya, Subhomoy Das

et al.

Topics in heterocyclic chemistry, Journal Year: 2015, Volume and Issue: unknown, P. 49 - 142

Published: Jan. 1, 2015

Language: Английский

Citations

46
Asymmetric [3 + 2] Cycloaddition of 2,2′-Diester Aziridines To Synthesize Pyrrolidine Derivatives DOI
Yuting Liao,

Baixin Zhou,

Yong Xia

et al.

ACS Catalysis, Journal Year: 2017, Volume and Issue: 7(6), P. 3934 - 3939

Published: May 4, 2017

A highly diastereo- and enantioselective [3 + 2] cycloaddition of 2,2′-diester aziridines with 3,4-dihydropyran derivatives acyclic enol ethers has been established. Various optically active octahydropyrano[2,3-c]pyrrole 3-methoxypyrrolidine were generated in moderate to high yields (up 94%) good stereoselectivities (>19:1 dr, up 95.5:4.5 er). The methodology was also applied the diastereoselective synthesis d-galactal derivatives. absolute configuration octahydropyrano[2,3-c]pyrroles showed that reactions using 6-alkyl-substituted ones as substrates gave reversed diastereoselection final cyclization step.

Language: Английский

Citations

40
Silver‐Catalyzed [3+2] Cycloaddition of Azomethine Ylides with Isocyanides for Imidazole Synthesis DOI

Zhongyan Hu,

Jinhuan Dong,

Xianxiu Xu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2017, Volume and Issue: 359(20), P. 3585 - 3591

Published: Aug. 14, 2017

Abstract A silver‐catalyzed aerobic oxidative [3+2] cycloaddition of azomethine ylides with aryl or heteroaryl isocyanides has been developed. The reaction represents a novel protocol for the efficient and practical synthesis 1,2‐diarylimidazoles bearing broad range substituents in good to excellent yields under mild conditions. practicability this was shown by gram‐scale double construction highly conjugated polyarylimidazole systems. magnified image

Language: Английский

Citations

36
Advances in synthesis and chemistry of azetidines DOI
Girija S. Singh

Advances in heterocyclic chemistry, Journal Year: 2019, Volume and Issue: unknown, P. 1 - 74

Published: Nov. 12, 2019

Language: Английский

Citations

31