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Usage

Uses

Used in Pharmaceutical Industry:
(S)-N¹,N¹-diethyl-3,3-dimethylbutane-1,2-diamine is used as a chiral building block for the synthesis of chiral drugs, leveraging its unique stereochemistry to create pharmaceuticals with specific biological activities. (S)-N¹,N¹-diethyl-3,3-dimethylbutane-1,2-diamine's ability to impart chirality is crucial for the development of drugs that target biological systems with high selectivity.
Used in Asymmetric Catalysis:
In the field of catalysis, (S)-N¹,N¹-diethyl-3,3-dimethylbutane-1,2-diamine is used as a chiral ligand for asymmetric catalysis. Its presence in catalytic systems enhances the selectivity of reactions, enabling the production of enantiomerically pure compounds, which is essential for the synthesis of biologically active molecules.
Used in Organic Synthesis:
(S)-N¹,N¹-diethyl-3,3-dimethylbutane-1,2-diamine serves as a versatile chiral resolving agent in organic synthesis. It is employed to resolve racemic mixtures into their individual enantiomers, which is vital for obtaining pure compounds with desired properties for various applications, including pharmaceuticals, agrochemicals, and fragrances.
Overall, (S)-N¹,N¹-diethyl-3,3-dimethylbutane-1,2-diamine is an important chemical compound with a wide range of applications in research and industry, particularly in the development of chiral molecules with specific biological and chemical properties.

Upstream product

• 26782-71-8 D-tert-leucine 
• 109-89-7 diethylamine 
• 340161-35-5 (S)-tert-butyl (1-(diethylamino)-3,3-dimethyl-1-oxobutan-2-yl)carbamate 
• 340161-31-1 (S)-2-amino-N,N-diethyl-3,3-dimethylbutanamide 
• 62965-35-9 N-tert-butyloxycarbonyl-L-tert-leucine 

Downstream Products

• 1602919-00-5 1-(3,5-bistrifluoromethylphenyl)-3-[(S)-1-diethylamino-3,3-dimethylbutan-2-yl]thiourea 

Relevant academic research and scientific papers

Access to Spirocyclic Benzothiophenones with Multiple Stereocenters via an Organocatalytic Cascade Reaction

The present report describes an organocatalytic cascade reaction between 2-alkylidene benzo[b]thiophenone derivatives and enones in the presence of the Cinchona alkaloid amine. Spirobenzothiophenonic cyclohexane derivatives containing three stereocenters were prepared via one-step synthesis in yields ranging from 88 to 96% and in enantioselectivities (enantiomeric excess (ee)) ranging from 85 to 97%, with diastereoselectivities of approximately 14/2/1. Therefore, this method provides an efficient route for the synthesis of a new class of optically active 2-spirobenzothiophenones.

Asymmetric Synthesis of Carbocyclic Propellanes

A modular synthesis of functionalized carbocyclic propellanes was developed. Formation of the first of two quaternary bridgehead centers has been achieved by desymmetrization of prostereogenic ketones by either Hajos-Parrish-Eder-Sauer-Wiechert-type processes or Werner’s catalytic asymmetric Wittig reaction. The obtained bicyclic enones were subjected to conjugate additions upon which the remaining ring was formed by olefin metathesis. All bridges are amenable to further derivatization, which renders those compounds useful as central units in fragment-based drug discovery or as ligand scaffolds.

A kind of T-leucine derivative of the chiral amine compound and its preparation method and application

The invention discloses a tertiary leucine derived chiral amine compound as well as a preparation method and application thereof. The chiral amine compound contains a tert-butyl group, a primary amine, a secondary amine or a tertiary amine functional group and has the structural formula as shown in the specification; and chiral amine and salts thereof are prepared through simple preparation steps by taking common tert-leucine as the raw material to form the chiral amine compound. The chiral amine and the salts thereof can be used for the asymmetrical Michael additive reaction between alpha, beta-unsaturated ketone and a nucleophilic reagent such as nitrocarbol, malonic ester, substituted oxazolone and the like and the asymmetrical cascade reaction between the alpha, beta-unsaturated ketone and fifth-position unsaturated rhodanine, between fifth-position unsaturated hydantoin and the alpha, beta-unsaturated ketone; and the tertiary leucine derived chiral amine compound has very high catalytic activity and stereoselectivity as well as the highest diastereoselectivity of 30/1 and the highest enantioselectivity of 99%, and is wide in oligomer range.

A practical protocol for asymmetric synthesis of wieland-miescher and hajos-parrish ketones catalyzed by a simple chiral primary amine

This article describes a simple chiral primary amine catalyzed efficient and practical protocol for the large-scale synthesis of Wieland-Miescher and Hajos-Parrish ketones as well as their analogues. Georg Thieme Verlag Stuttgart. New York.

Chiral primary amine catalyzed asymmetric direct cross-aldol reaction of acetaldehyde

The first primary aminocatalytic direct cross-aldol reaction of acetaldehyde is presented. Among the various vicinal diamines screened, the L-tert-leucine derivative 1c in conjunction with (H4SiW 12O40)0.25 was identified as the optimal catalyst; good catalytic activity (up to 99% yield in 4 h), and high enantioselectivities (up to 92% ee) were achieved for a range of donors, including aromatic aldehydes and isatin derivatives. Aqueous acetaldehyde solution and paraldehyde can be conveniently applied in this system.