N‐Heterocyclic Carbene‐Catalyzed Atroposelective Synthesis of 5‐Indo‐1‐yl Pyran‐2‐ones with an N−C axis from Enals

Zhang, Linxue; Wu, Qianqian; Ren, Min; Zhang, Hailong; Zhang, Xiaoxiang; Liu, Jinhua; Fu, Zhenqian

doi:10.1002/adsc.202300686

Cited by 3 publications

(2 citation statements)

References 69 publications

(18 reference statements)

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“…In the NHC catalysis, the α,β-unsaturated acyl azoliums are Michael acceptors acting as a C3 synthon for [3 + 3] annulation [86][87][88][89][90][91][92][93][94][95][96][97][98]. The oxidative reactions of β-cyano-substituted α, β-unsaturated aldehyde 31 and ethyl acetoacetate 32 were studied (Scheme 8) [90].…”

Section: [3 + 3] Annulationmentioning

confidence: 99%

“…Next, the Michael addition of 32 to acyl azolium intermediate and the subsequent lactonization provide the annulation product 33, accompanied by the liberation of the NHC catalyst. The asymmetric synthesis of axially chiral molecules was achieved via oxidative [3 + 3] annulation [97]. The chiral NHC-catalyzed oxidative annulation of cinnamaldehyde 5 and indole-1-pyruvate ester 34 gave the N-arylindole 35 with a C-N chiral axis.…”

Section: [3 + 3] Annulationmentioning

confidence: 99%

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NHC-Catalyzed Reaction of Aldehydes for C(sp2)–O Bond Formation

Yamaoka,

Miyabe

2024

Catalysts

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In the past few decades, N-heterocyclic carbenes (NHCs) have opened the new field of organocatalysis in synthetic organic chemistry. This review highlights the dramatic progress in the field of NHC-catalyzed C–O bond formation based on the activation of aldehyde C(sp2)–H bonds. The oxidative and redox transformations for the synthesis of various molecules with structural diversity and complexity are summarized. Furthermore, new methods and strategies for NHC catalysis are emerging continuously; thus, cooperative catalysis with Brønsted acid, hydrogen-bonding catalyst, transition-metal catalyst, and photocatalyst are also described.

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Section: [3 + 3] Annulationmentioning

confidence: 99%

Section: [3 + 3] Annulationmentioning

confidence: 99%

NHC-Catalyzed Reaction of Aldehydes for C(sp2)–O Bond Formation

Yamaoka,

Miyabe

2024

Catalysts

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Current Developments in Michael Addition Reaction using Heterocycles as Convenient Michael Donors

Samanta,

Shankar Panda,

Mohapatra

et al. 2024

Asian J Org Chem

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The Michael addition reaction, a cornerstone of contemporary organic synthesis, has witnessed a resurgence of interest owing to its ability to forge intricate carbon‐carbon and carbon‐heteroatom bonds. In the past few years, heterocyclic compounds have been rigorously used as Michael donors, owing to their architectural diversity and distinct reactivity with or without the presence of base/transition metals/organocatalysts. This review encapsulates the latest breakthroughs in chemistry involving Michael addition reaction using heterocyclic compounds as Michael donors. It delivers a comprehensive update on developments in Michael addition reaction triggered by potent heterocycles since 2017, highlighting novel and innovative methodologies, with strategic insights.

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Catalytic Asymmetric Diastereodivergent Synthesis of 2-Alkenylindoles Bearing both Axial and Central Chirality

Yang,

Huang,

Wang

et al. 2024

Precision Chemistry

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The catalytic asymmetric diastereodivergent synthesis of axially chiral 2-alkenylindoles was established via chiral phosphoric acid-catalyzed addition reactions of C3-unsubstituted 2-alkenylindoles with o-hydroxybenzyl alcohols under different reaction conditions. Using this strategy, two series of 2-alkenylindoles bearing both axial and central chirality were synthesized in a diastereodivergent fashion with moderate to high yields and good stereoselectivities (up to 99% yield, 95:5 er, >95:5 dr). Moreover, theoretical calculations were performed on the key transition states leading to different stereoisomers, which provided an in-depth understanding of the origin of the observed stereoselectivity and diastereodivergence of the products under different reaction conditions. More importantly, these 2-alkenylindoles were utilized in asymmetric catalysis as chiral organocatalysts and in medicinal chemistry for evaluation of their cytotoxicity, which demonstrated their potential applications. This study has not only established the catalytic atroposelective synthesis of axially chiral 2-alkenylindoles, but also provided an efficient strategy for catalytic asymmetric diastereodivergent construction of indole-based scaffolds bearing both axial and central chirality.

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N‐Heterocyclic Carbene‐Catalyzed Atroposelective Synthesis of 5‐Indo‐1‐yl Pyran‐2‐ones with an N−C axis from Enals

Cited by 3 publications

References 69 publications

NHC-Catalyzed Reaction of Aldehydes for C(sp2)–O Bond Formation

NHC-Catalyzed Reaction of Aldehydes for C(sp2)–O Bond Formation

Current Developments in Michael Addition Reaction using Heterocycles as Convenient Michael Donors

Catalytic Asymmetric Diastereodivergent Synthesis of 2-Alkenylindoles Bearing both Axial and Central Chirality

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