Diastereoselective Synthesis of Cyclic Five‐Membered <i>trans</i>,<i>trans</i>‐Configured Nitrodiols by Double Henry Reaction of 1,4‐Dialdehydes

Fröhlich, Janine; Lehmkuhl, Kirstin; Fröhlich, Roland; Wünsch, Bernhard

doi:10.1002/ardp.201500114

Cited by 3 publications

(1 citation statement)

References 32 publications

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“…4-Oxo-2-nonenal (ONE) was synthesized from 2pentylfuran according to a previous study (55). 1,4-Butanedial (BDA) was synthesized from 2,5dimethoxytetrahydrofuran according to a previously described method (56). Malondialdehyde (MDA) was synthesized from 1,1,3,3tetramethoxypropane according to a previous study (57).…”

Section: J O U R N a L P R E -P R O O Fmentioning

confidence: 99%

Unique B-1 cells specific for both N-pyrrolated proteins and DNA evolve with apolipoprotein E deficiency

Lim

Yamaguchi

Itakura

et al. 2022

Journal of Biological Chemistry

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This is a PDF file of an article that has undergone enhancements after acceptance, such as the addition of a cover page and metadata, and formatting for readability, but it is not yet the definitive version of record. This version will undergo additional copyediting, typesetting and review before it is published in its final form, but we are providing this version to give early visibility of the article. Please note that, during the production process, errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain.

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Section: J O U R N a L P R E -P R O O Fmentioning

confidence: 99%

Unique B-1 cells specific for both N-pyrrolated proteins and DNA evolve with apolipoprotein E deficiency

Lim

Yamaguchi

Itakura

et al. 2022

Journal of Biological Chemistry

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Domino Reactions through Recursive Anionic Cascades: The Advantageous Use of Nitronates

2022

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Recursive Anionic Cyclization (RAC) continues to proliferate as a mechanistically distinct domino strategy. Deployment of nitroalkanes as a source of recursive carbanions has created a niche operating space for generating molecular complexity and diversity. This new corollary i. e. recursive nitronate cyclization is the basis of a domino [5 C+1 C] cyclization strategy wherein nitroalkanes act as one‐carbon lynchpin, providing rapid access to topologically intriguing, densely functionalized carbo‐ and heterocycles embodying multiple chiral centers with regio‐, stereo‐ and enantioselectivity. Extension to aromatic domains, particularly via benzannulation reactions, has further consolidated the operating space. While leveraging the functional versatility of nitro group for post‐domino modifications, such endeavors have culminated in total synthesis of diverse natural products. An incisive analysis of recursive nitronate cyclizations and their emergent potentials is delineated in this review. It is hoped that this focused narrative will enthuse and draw new practitioners to the arena to advance the field.

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A Kinetic Study of the Intramolecular Nitroaldol (Henry) Reaction Giving 2‐Nitroindan‐1‐ols

et al. 2019

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An intramolecular base-catalyzed nitroaldol reaction of three newly prepared 2-(2-nitroalkyl)benzaldehydes (1a-c) giving corresponding 2-nitroindan-1-ols (2a-c) was studied in water and five non-aqueous solvents. Whilst for the parent 2-(2nitroethyl)benzaldehyde (1a) the reaction takes place in two kinetically discernible steps -deprotonation and cyclization, for 2-(2-nitropropyl)-and 2-(2-nitro-2-phenylethyl)benzaldehydes 1b and 1c general base-catalyzed formation of a reactive carbanion is rate-limitting. An unusually high Brønsted coef-ficient (β B = 1.12 � 0.03) was found for 1b indicating smaller imbalance of the transition state whose structure therefore resembles a nitronate. Cyclization products 2a-c prefer relative trans-configuration in ratios from 55:45 to 83:17 depending on the solvent. Mutual interconversion of the cis-/trans-diastereoisomers occurs either via nitronate species 2aor via a reverse ring opening/ring closing pathway through the nitronate species 1band 1c -. The mechanism was also supported by quantum calculations.

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Diastereoselective Synthesis of Cyclic Five‐Membered trans,trans‐Configured Nitrodiols by Double Henry Reaction of 1,4‐Dialdehydes

Cited by 3 publications

References 32 publications

Unique B-1 cells specific for both N-pyrrolated proteins and DNA evolve with apolipoprotein E deficiency

Unique B-1 cells specific for both N-pyrrolated proteins and DNA evolve with apolipoprotein E deficiency

Domino Reactions through Recursive Anionic Cascades: The Advantageous Use of Nitronates

A Kinetic Study of the Intramolecular Nitroaldol (Henry) Reaction Giving 2‐Nitroindan‐1‐ols

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