53561-77-6

Upstream product

• 917-54-4 methyllithium 
• 528819-08-1 N-[(1E)-2,2-dimethylpropylidene]-[(4R,5R)-4,5-diphenyl-1,3-dioxolan-2-yl]amine 
• 1164111-52-7 C₆H₁₃N*ClH 
• 1089728-85-7 C₁₀H₂₁NOS 
• 221375-58-2 (R_S)-N-(3,3-dimethylbutan-2-ylidene)-2-methylpropane-2-sulfinamide 
• 75-97-8 3,3-dimethyl-butan-2-one 
• 911372-73-1 (R_S)-N-((R)-3,3-dimethylbutan-2-yl)-2-methylpropane-2-sulfinamide 
• 558-37-2 tert-butylethylene 
• 85231-76-1 N-(3,3-dimethyl-2-butyl)-phosphoramidate 
• 917-92-0 3,3-Dimethylbut-1-yne 

Downstream Products

• 85371-64-8 N-cyano-N''-(pyridin-4-yl)-N'-(1,2,2-trimethylpropyl)guanidine 
• 874212-56-3 C₁₃H₁₉NO 

Relevant academic research and scientific papers

Synthesis method of primary amine hydrochloride

The invention discloses a synthesis method of primary amine hydrochloride. According to the synthesis method, in the presence of a gold complex, water and alkyne carry out catalytic hydrolysis to generate ketones, and then ketones and ammonium formate are catalyzed by a rhodium complex to generate primary amine. Compared with a conventional primary amine synthesis method, the synthesis method hasthe advantages that no alkali is added during the reaction process, no side product is generated, the atomic economy is good, the reaction conditions are mild, and the synthesis method has a wide prospect.

Asymmetric Reduction of tert-Butanesulfinyl Ketimines by N-Heterocyclic Carbene Boranes

N-heterocyclic carbene borane (NHC-borane) based on a triazole core is demonstrated for the first time to be efficient for reduction of a variety of tert-butanesulfinyl ketimines. Up to 95% yield and up to >99% diastereomeric excess were achieved. NHC-borane exhibited excellent activities that are more efficient than or comparable to commonly used reductive reagents such as NaBH4, NaBH3CN, l-selectride, Ru catalyst, or BH3-THF.

Microwave-Enhanced Asymmetric Transfer Hydrogenation of N-(tert-Butylsulfinyl)imines

Microwave irradiation has considerably enhanced the efficiency of the asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)imines in isopropyl alcohol catalyzed by a ruthenium complex bearing the achiral ligand 2-amino-2-methylpropan-1-ol. In addition to shortening reaction times for the transfer hydrogenation processes to only 30 min, the amounts of ruthenium catalyst and isopropyl alcohol can be considerably reduced in comparison with our previous procedure assisted by conventional heating, which diminishes the environmental impact of this new protocol. This methodology can be applied to aromatic, heteroaromatic and aliphatic N-(tert-butylsulfinyl)ketimines, leading, after desulfinylation, to the expected primary amines in excellent yields and with enantiomeric excesses of up to 96 %. Microwave irradiation promotes the asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)imines in 2-propanol catalysed by a ruthenium complex bearing an achiral β-amino alcohol as ligand. After desulfinylation, α-branched primary amines containing aromatic, heteroaromatic and aliphatic substituents are obtained in excellent yields and with enantiomeric excesses of up to 96 %.

A versatile Ru catalyst for the asymmetric transfer hydrogenation of both aromatic and aliphatic sulfinylimines

A highly efficient Ru catalyst based on an achiral, very simple, and inexpensive amino alcohol ligand (2-amino-2-methylpropan-1-ol) has been developed for the asymmetric transfer hydrogenation (ATH) of chiral N-(tert-butylsulfinyl)imines. This complex is able to catalyze the ATH of both aromatic and the most challenging aliphatic sulfinylimines by using isopropyl alcohol as the hydrogen source. The diastereoselective reduction of aromatic, heteroaromatic, and aliphatic sulfinylketimines, including sterically congested cases, over short reaction times (1-4 h), followed by desulfinylation of the nitrogen atom, affords the corresponding highly enantiomerically enriched (ee up to >99%) α-branched primary amines in excellent yields. The same ligand was equally effective for the synthesis of both (R)- and (S)-amines by using the appropriate absolute configuration in the iminic substrate. DFT mechanistic studies show that the hydrogen-transfer process is stepwise. Moreover, the origin of the diastereoselectivity has been rationalized.

Enantioselective hydrogenation of N-H imines

(Figure Presented) N-H ketoimines 3a-3v are readily prepared in high yield via organometallic addition to nitriles and isolated as corresponding bench-stable hydrochloride salts. Homogeneous asymmetric hydrogenation of unprotected N-H ketoimines 3a-3v usi

One-pot asymmetric synthesis of either diastereomer of tert-butanesulfinyl- protected amines from ketones

A one-pot method for the asymmetric synthesis of tert-butanesulfinyl- protected amines is described. Condensation of aryl alkyl and dialkyl ketones with tert-butanesulfinamide followed by in situ reduction with the appropriate reagent provides either dias

Reversal of diastereofacial selectivity in hydride reductions of N-tert-butanesulfinyl imines

A variety of N-tert-butanesulfinyl imines were reduced with NaBH 4 in THF containing 2% water to provide the corresponding secondary sulfinamides in high yield and diastereoselectivity. By using the same sulfinyl imine starting materials and changing the reductant to L-Selectride, the stereoselectivity could be efficiently reversed to afford the opposite product diastereomer in high yield and selectivity.

Orthoacylimines: A new class of chiral auxiliaries for nucleophilic addition of organolithium reagents to imines

A new class of orthoacylimine-derived chiral auxiliaries has been synthesized and tested in the nucleophilic addition of organolithium reagents to imines. The precursors can be prepared by an aza-Wittig reaction between the corresponding orthoacyl azide and a variety of aldehydes in the presence of trialkylphosphines. The nucleophilic addition of organolithium reagents led to the addition products in good yields and with good to excellent diastereoselectivities (from 85:15 to 99:1). The chiral, nonracemic secondary amines could be readily obtained under mild hydrolytic condition. Furthermore, the chiral auxiliary can be recovered in quantitative yield and reconverted to the starting orthoacyl azide precursor. This method was applied to the synthesis of (S)-t-leucine.