Synthesis and Applications of β-Aminocarboxylic Acids Containing a Cyclopropane Ring

Gnad, Frieder; Reiser, Oliver

doi:10.1021/cr010015v

Cited by 311 publications

(88 citation statements)

References 120 publications

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“…[29][30][31][32][33] This interesting moiety is also present in biologically active compounds, as natural and synthetic cyclopropanes are endowed with a large range of biological properties, such as enzyme inhibition, insecticidal, antifungal, herbicidal, antimicrobial, antibiotic, antibacterial, antitumor and antiviral activities. 34 The history of cyclopropanations of furans started already more than two decades ago.…”

Section: B Main Partmentioning

confidence: 99%

Enantioselective synthesis of (−)-paeonilide

Harrar

Reiser

2012

Chem. Commun.

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Section: B Main Partmentioning

confidence: 99%

Enantioselective synthesis of (−)-paeonilide

Harrar

Reiser

2012

Chem. Commun.

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“…Asymmetric Synthesis of 2-Nitrocyclopropanecarboxylic Acids 2-Nitrocyclopropanecarboxylic acid derivatives are recognized as versatile precursors for biologically active compounds [126][127][128][129] as well as useful building blocks for the synthesis of highly functionalized molecular targets. [130][131][132][133] Therefore catalytic and enantioselective construction of these motifs is a valuable challenge for synthetic chemists. Asymmetric Michael addition followed by intramolecular nucleophilic substitution is a representative process for this purpose.…”

Section: )mentioning

confidence: 99%

Development of Chiral Thiourea Catalysts and Its Application to Asymmetric Catalytic Reactions

2010

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We have developed several multifunctional thiourea catalysts bearing a tertiary amine or an 1,2-amino alcohol in expectation of their synchronous activation of a nucleophile and an electrophile through both acid-base and hydrogen-bonding interactions. From these studies, it was revealed that the weak acidity of thioureas compared with metallic Lewis acids could be overcome by this modification. The bifunctional aminothiourea could be used efficiently for a wide range of diastereoselective and enantioselective nucleophilic reactions such as Michael addition of 1,3-dicarbonyl compounds to nitroolefines, aza-Henry reaction of nitroalkanes to N-Boc imines, and hydrazination of cyclic b b-keto esters. We also discovered that multifunctional thiourea catalyst, bearing an 1,2-amino alcohol moiety, significantly accelerated the Petasis-type reaction of alkenylboronic acids to Nphenoxycarbonyl quinolinium salts, prepared from quinolines and phenyl chloroformate, to afford 1,2-addition products with high enantioselectivity (up to 97% ee). Furthermore, to expand the synthetic applicability of the thiourea-catalyzed asymmetric reactions, tandem organocatalyzed reactions were explored to establish the concise one-pot synthesis of chiral densely functionalized three-, five-, and six-membered compounds.

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“…[1][2][3][4] It is present in a number of relevant compounds, [5][6][7] it produces unusual structures, [8][9][10] and it is part of many versatile synthetic intermediates. [11,12] Substituted cyclopropane rings are potentially chiral, and their enantioselective synthesis has been the subject of intense research in recent years.…”

Section: Introductionmentioning

confidence: 99%

DFT/MM Study on Copper‐Catalyzed Cyclopropanation – Enantioselectivity with No Enthalpy Barrier

Drudis-Solé¹,

Maseras²,

Lledós³

et al. 2008

Eur J Org Chem

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The enantioselectivity in the reaction of [Cu(adam‐box)(CHCO2Me)] {adam‐box = 2,2′‐isopropylidenebis[(4R)‐(1‐adamantyl)‐2‐oxazoline]} with Ph2C=CH2 was analyzed computationally by ONIOM(B3LYP:UFF) calculations. The lack of transition states in the potential‐energy surface precludes the use of conventional approaches and requires the definition of reaction paths in an approximate Gibbs free‐energy surface. The procedure is time consuming and intrinsically less accurate than the usual approaches based on enthalpic energy surfaces, but it produces results in reasonable agreement with experiment, which furthermore allow identification of the key interactions responsible for chiral discrimination.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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Synthesis and Applications of β-Aminocarboxylic Acids Containing a Cyclopropane Ring

Cited by 311 publications

References 120 publications

Enantioselective synthesis of (−)-paeonilide

Enantioselective synthesis of (−)-paeonilide

Development of Chiral Thiourea Catalysts and Its Application to Asymmetric Catalytic Reactions

DFT/MM Study on Copper‐Catalyzed Cyclopropanation – Enantioselectivity with No Enthalpy Barrier

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