Direct Organo-Catalytic Asymmetricα-Amination of Aldehydes—A Simple Approach to Optically Activeα-Amino Aldehydes,α-Amino Alcohols, andα-Amino Acids

Bøgevig, Anders; Juhl, Karsten; Kumaragurubaran, Nagaswamy; Zhuang, Wei; Jørgensen, Karl Anker

doi:10.1002/1521-3773(20020517)41:10<1790::aid-anie1790>3.0.co;2-y

Cited by 464 publications

(137 citation statements)

References 40 publications

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“…Intermediate Schiff base 161 undergoes intramolecular cyclization with participation of the secondary amino group [159] (Scheme 55). This procedure was used to obtain for the first time derivatives of imidazo[1,2-c]quinazoline [160], 1H-perimidine [161], thieno[2′,3′ : 4,5]pyrimido-[1,6-a]benzimidazole [162], quinazolin-4(3H)-one [159,[163][164][165], and 1,3a,5,7-tetraazabenzo[a]cyclopenta[h]anthracene [166]. High anxiolytic activity of isoxazolo [4,5-d]pyrimidine-3,7-dione was noted [167]; it exceeded the activity of widely used diazepam.…”

Section: Scheme 37mentioning

confidence: 99%

Aliphatic aldehydes in the synthesis of carbo- and heterocycles: Part II. Synthesis of six- and seven-membered rings, bicyclic compounds, and macrocycles

Dyachenko

Karpov

2011

Russ J Org Chem

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Section: Scheme 37mentioning

confidence: 99%

Aliphatic aldehydes in the synthesis of carbo- and heterocycles: Part II. Synthesis of six- and seven-membered rings, bicyclic compounds, and macrocycles

Dyachenko

Karpov

2011

Russ J Org Chem

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“…The development of a direct asymmetric organocatalytic a-amination reaction for aldehydes was independently reported by List [65] and Jørgensen [66]. Interest in this reaction stems from the versatile products that can be produced, such as amino alcohols, a-amino acids, and 4-substituted oxazolidinone compounds.…”

Section: A-amination Reactionmentioning

confidence: 99%

“…The 2-hydrazino alcohols were transformed into 4-substituted oxazolidinone compounds by hydrogenation over Raney nickel and subsequent condensation with phosgene.Jørgensen et al also obtained a-aminated products of aldehydes in good yields and with excellent enantioselectivities (Scheme 7.35). Reduction and subsequent cyclization of the a-amino aldehyde products directly gave the N-aminooxazolidinones[66].…”

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confidence: 99%

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Catalysis of Reactions by Amino Acids

Xie

Hayes

Gathergood

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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j283 processes (Figure 7.2) [8]. As a result, proline has been studied as an effective catalyst and investigated for several powerful asymmetric transformations, such as the Aldol, Mannich, and Michael reactions. In addition, to provide opportunities for a better understanding of the origin of homochirality [9][10][11], amino acids as fundamental building blocks of organisms need to be investigated for their possible asymmetric transformation and amplification into prebiotic units such as sugars.Although amino acids, especially (S)-proline, have shown high efficiency in many valuable organic transformations affording corresponding products with high regio-, diastereo-, and enantioselectivities, sometimes such transformations suffered drawbacks. These include high catalyst loading, excess of nucleophile, long reaction times, and low solubility of catalyst in organic reaction media. To overcome these drawbacks and improve the catalytic performance of proline, some modifications to the structure of (S)-proline have been reported, thus allowing the fine-tuning of catalytic properties and improving the activities and conditions. Illustrated examples of modified amino acids are included in this chapter; however, several excellent recent reviews cover these derivatives in more detail [9-11].Scheme 7.2 Hajos-Parrish-Eder-Sauer-Wiechert reactions. Aldol Reaction j285Scheme 7.4 Organocatalytic transformation of 1,3-diketones into optically active cyclohexanones. 286j 7 Catalysis of Reactions by Amino Acids R 2 = Me, Et R 3 = H, Me Scheme 7.6 Asymmetric organocatalytic synthesis of cissubstituted dihydrobenzofuranols via intramolecular Aldol reactions. 7.2 Aldol Reaction j287 288j 7 Catalysis of Reactions by Amino Acids R 1 Scheme 7.9 (S)-Proline-catalyzed intermolecular Aldol reactions.290j 7 Catalysis of Reactions by Amino Acids Scheme 7.11 Organocatalytic enantioselective synthesis of a-hydroxy phosphonates. Aldol Reaction j291Scheme 7.14 Proline-catalyzed intermolecular Aldol reaction. Aldol Reaction j293Scheme 7.15 Two-step carbohydrate synthesis: iterative aldehyde aldol.294j 7 Catalysis of Reactions by Amino Acids D-sugars in most cases with >99% e.e. This two-step Aldol strategy opens up a novel route to enantiomerically pure d-lactones from simple aldehydes. For example, the hexoses obtained can be quantitatively converted into d-lactones by oxidation with MnO 2 (Scheme 7.18).

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“…Recently, the catalytic property of L-proline was observed to have broad activity in aldol- [4][5][6], Mannich- [7][8][9], Michael- [10,11], Diels-Alder- [12][13][14], a-amination reactions and Knoevenagel reactions [15,16].…”

Section: Introductionmentioning

confidence: 99%

Three-component synthesis of novel trifluoromethyl-containing tetrahydropyran derivatives

Zhang

Cao

et al. 2009

Journal of Fluorine Chemistry

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Direct Organo-Catalytic Asymmetricα-Amination of Aldehydes—A Simple Approach to Optically Activeα-Amino Aldehydes,α-Amino Alcohols, andα-Amino Acids

Cited by 464 publications

References 40 publications

Aliphatic aldehydes in the synthesis of carbo- and heterocycles: Part II. Synthesis of six- and seven-membered rings, bicyclic compounds, and macrocycles

Aliphatic aldehydes in the synthesis of carbo- and heterocycles: Part II. Synthesis of six- and seven-membered rings, bicyclic compounds, and macrocycles

Catalysis of Reactions by Amino Acids

Three-component synthesis of novel trifluoromethyl-containing tetrahydropyran derivatives

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