Primary-secondary Diamine Research Articles

Primary-Secondary Diamine Catalyzed Enantioselective Synthesis of Substituted Cyclohex-2-enones by Cascade Michael–Aldol–­Dehydration of Ketones with Chalcones

A simple primary-secondary diamine organocatalyst catalyzes the cascade Michael–aldol–dehydration of chalcones and unmodified ketones to produce substituted cyclohex-2-enones under mild conditions with good yields and high enantio- and/or diastereoselectivities. The success of the catalyst system is possibly due to simultaneous activation of the electrophilic chalcone by iminium formation and the nu­cleophilic ketone by enamine formation with an overall intramolecular iminium–di-enamine mechanism.

N-Acyl-N-(4-chlorophenyl)-4-nitrobenzenesulfonamides: highly selective and efficient reagents for acylation of amines in water

Abstract A variety of N-acyl-N-(4-chlorophenyl)-4-nitrobenzenesulfonamides (1a–e) were synthesized in one pot from 4-chloroaniline under solvent-free conditions and have been developed as chemoselective N-acylation reagents. Selective protection of primary amines in the presence of secondary amines, acylation of aliphatic amines in the presence of aryl amines, and monofunctionalization of primary-secondary diamines as well as selective N-acylation of amino alcohols using these reagents are described. All of the acylation reactions were carried out in water as a green solvent. High stability and easy preparation of these acylating reagents are other advantages of this method.

Primary-secondary diamines catalyzed Michael reaction to generate chiral fluorinated quaternary carbon centers

Asymmetric Michael reactions of α-fluoro-β-ketoesters to nitroolefins have been achieved by using readily accessible primary-secondary diamines as the organocatalysts through enamine activation mode, affording the useful Michael adducts bearing chiral fluorinated quaternary carbon in good yields, with high diastereoselectivities and enantioselectivities (up to 87% yield, >20:1 d.r. and 99% ee).

Asymmetric Robinson-type annulation reaction between β-ketoamides and α,β-unsaturated ketones.

Enantioselective Robinson-type annulation reaction between β-ketoamide and α,β-unsaturated ketone was developed by utilizing the amino acid derived primary-secondary diamine catalysts. The less reactive acyclic β-ketoamides employed as both electrophile and nucleophile are reported in this asymmetric tandem reaction. A number of chiral cyclohexenone derivatives containing an amide group were obtained in high yields and good selectivities.

Asymmetric domino Michael–aldol reactions catalyzed by recyclable PEG supported chiral primary aminoalcohol and primary–secondary diamine catalysts in water

PEG supported chiral primary aminoalcohol and primary–secondary diamine have been synthesized and used to catalyze the asymmetric domino Michael–aldol reactions of benzyl benzoylacetate and α,β-unsaturated ketones in water to afford optically active cyclohexanones. Excellent diastereoselectivities, good to excellent enantioselectivities and good yields were obtained, and catalyst recycling was accompanied by almost intact diastereo- and enantioselectivity and some loss of the chemical efficiency.

Determination of Acrylamide in Fried Foods Based on QuEChERS-HPLC Method

A simple and rapid method based on QuEChERS( quick,easy,cheap,effective,rugged and safe)-HPLC technology for the determination of acrylamide( AAM) in fried food was developed. The advantage of this method lies in that the pure water is used directly to eliminate the interference of sample base without introducing organic solvents in the modified QuEChERS method. With this method,AAM in samples was extracted with pure water using ultrasonic bath and cleaned up by primary secondary diamine( PSA). To determine the content of AAM,a C18column with water-acetonitrile( V / V = 1∶ 99) as eluent and a UV detector adjusted at 208 nm were employed in HPLC. Under the optimal experiment conditions,there is a good linear relationship( r = 0. 9994) in the concentration range of 0. 020 ~ 0. 800 μg / g and the detection limit of AAM is 0. 005 μg / g. The recoveries of AAM in samples are in the range of 83. 96% ~ 89. 43%,with relative standard deviations( RSD) of 2. 13% ~ 5. 87%. The developed method is proved to be simple,reliable and sensitive for fast determination of AAM in fried food such as instant noodles.

ChemInform Abstract: Organocatalytic Asymmetric Michael Addition of Ethyl Nitroacetate to Enones Using Natural Amino Acids‐Derived C1‐Symmetric Chiral Primary—Secondary Diamines.

AbstractAn optimal catalyst system is elaborated for the synthesis of various chiral γ‐nitroketone adducts, which represent important building blocks.

Synthesis of C 1-symmetric primary-secondary diamines and their application in the enantioselective Henry reaction

Two new C1-symmetric primary-secondary diamines were synthesized via the reaction of (S,S)-1,2-diphenyl ethylene diamine with 3,5-ditert-butyl salicylaldehyde and salicylaldehyde, respectively, followed by reduction with NaBH4. The combination of the ligand from 3,5-ditert-butyl salicylaldehyde with CuBr could effciently catalyze the Henry reaction to afford β-nitroalkanols in moderate to good yields (up to 87%) and high enantioselectivities (up to 88% ee). A possible mechanism of the reaction was proposed.

Asymmetric Intramolecular Oxa-Michael Reactions to Tetrahydrofurans/2H-Pyrans Catalyzed by Primary–Secondary Diamines

The asymmetric intramolecular oxa-Michael reactions of α,β-unsaturated ketones have been achieved by using readily accessible primary–secondary diamines as the organocatalysts, giving the synthetically useful tetrahydrofurans/2H-pyrans in good yields and with high enantioselectivities (up to 90% ee).

Organocatalytic asymmetric Michael addition of ethyl nitroacetate to enones using natural amino acids-derived C1-symmetric chiral primary–secondary diamines

A highly organocatalytic asymmetric Michael addition of ethyl nitroacetate to enones by using C1-symmetric chiral primary–secondary diamines has been developed. In assistance of o-nitrobenzoic acid, chiral amine 1f which was derived from l-tryptophane and d-camphor can effectively promote the transformation in high yields (up to 96%) and enantioselectivities (up to 95%) under mild conditions.

ChemInform Abstract: Facile Creation of 2‐Substituted Indolin‐3‐ones by Using Primary—Secondary Diamine Catalysts.

AbstractThe asymmetric organocatalytic conjugate addition of acetylindolinone to enones constitutes an easy and efficient method for the direct preparation of substituted indolinones.

Facile Creation of 2‐Substituted Indolin‐3‐ones by Using Primary–Secondary Diamine Catalysts

The asymmetric organocatalytic conjugate addition of acetylindolinone to enones constitutes an easy and efficient method for the direct preparation of substituted indolinones.

Asymmetric Crossed‐Conjugate Addition of Nitroalkenes to Enones by a Chiral Bifunctional Diamine Organocatalyst

An easily available new type of primary-secondary diamine catalyst promotes the title reaction with yields of up to 96% and enantioselectivities of up to 99% e.e.

Water-Compatible Iminium Activation: Highly Enantioselective Organocatalytic Michael Addition of Malonates to α,β-Unsaturated Enones

The highly enantioselective Michael addition of malonates to α,β-unsaturated ketones in water was reported to be catalyzed by a primary-secondary diamine catalyst containing a long alkyl chain. This asymmetric Michael addition process was found to be effective for a variety of α,β-unsaturated ketones.

ChemInform Abstract: Organocatalyzed Enantioselective Michael Additions of Nitroalkanes to Enones by Using Primary—Secondary Diamine Catalysts.

AbstractThe title reaction affords the corresponding Michael adducts with high yields and enantioselectivities.

ChemInform Abstract: Enantioselective Synthesis of Functionalized Fluorinated Cyclohexenones via Robinson Annulation Catalyzed by Primary—Secondary Diamines.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Chiral Primary—Secondary Diamines Catalyzed Michael—Aldol—Dehydration Reaction Between Benzoylacetates and α,β‐Unsaturated Ketones: Highly Enantioselective Synthesis of Functionalized Chiral Cyclohexenones.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Enantioselective Friedel—Crafts Alkylation of 4,7‐Dihydroindoles with Enones Catalyzed by Primary—Secondary Diamines.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Organocatalyzed enantioselective Michael additions of nitroalkanes to enones by using primary–secondary diamine catalysts

Primary-secondary diamines perform as efficient organocatalysts for the asymmetric addition of nitroalkanes to enones, giving the Michael adducts with excellent yields and enantioselectivities.

Chiral Primary–Secondary Diamines Catalyzed Michael–Aldol–Dehydration Reaction between Benzoylacetates and α,β‐Unsaturated Ketones: Highly Enantioselective Synthesis of Functionalized Chiral Cyclohexenones

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