127611-91-0

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 

Downstream Products

• 215731-62-7 (R)-ethyl 3-(N-((R)-1-phenylethyl)amino)pentanoate 
• 169214-05-5 (3S,αR)-ethyl 3--4-methylpentanoate 

Relevant academic research and scientific papers

The application of high-throughput synthesis and purification to the preparation of ethanolamines

A 48 compound library of structurally diverse ethanolamines was prepared using a parallel synthesis approach. The synthetic paradigm employed a solution phase epoxide-opening reaction followed by rapid purification by ion exchange chromatography to yield

Synthesis of enantiopure 1,3,4-thiazaphospholes

Racemic and (R)-(+)-N-trimethylsilyl-(1-phenyl)ethylamines stereoselectively react with O-phenylchloromethylisothiocyanatothiophosphonate to give a diastereomeric mixture of separable 1,3,4-thiazaphospholes; racemic thiazaphosphole crystallises as a congl

Hypervalent Iodine(III) Reagents with Transferable Primary Amines: Structure and Reactivity on the Electrophilic α-Amination of Stabilized Enolates

A new family of hypervalent iodine reagents containing transferable primary amine groups is described. Benziodoxolone-based reagents were synthesized on the gram-scale through operationally simple reactions in up to quantitative yields. These bench-stable solids were characterized by X-ray analysis and successfully employed in the α-amination of indanone-based β-ketoesters in up to 83% yield. Mechanistic studies indicate a substitution mechanism involving an electrophilic amine.

Synthesis of Urea Derivatives from CO2 and Silylamines

A series of thirty-three N,N′-diaryl, dialkyl, and alkyl-aryl ureas have been prepared in pyridine or toluene by reaction of silylamines with CO2. This protocol is shown to provide facile access to 13C-labeled ureas, as well as chiral and macrocyclic ureas. These reactions proceed through initial generation of the corresponding silylcarbamates, which subsequently react with silylamine under thermal conditions to afford the thermodynamically favored urea and disilyl ether.

Modulation of multifunctional N,O,P ligands for enantioselective copper-catalyzed conjugate addition of diethylzinc and trapping of the zinc enolate

In this work, we have successfully synthesized a new family of chiral Schiff base-phosphine ligands derived from chiral binaphthol (BINOL) and chiral primary amine. The controllable synthesis of a novel hexadentate and tetradentate N,O,P ligand that contains both axial and sp3-central chirality from axial BINOL and sp3-central primary amine led to the establishment of an efficient multifunctional N,O,P ligand for copper-catalyzed conjugate addition of an organozinc reagent. In the asymmetric conjugate reaction of organozinc reagents to enones, the polymer-like bimetallic multinuclear Cu-Zn complex constructed in situ was found to be substrate-selective and a highly excellent catalyst for diethylzinc reagents in terms of enantioselectivity (up to >99 % ee). More importantly, the chirality matching between different chiral sources, C2-axial binaphthol and sp3-central chiral phosphine, was crucial to the enantioselective induction in this reaction. The experimental results indicated that our chiral ligand (R,S,S)-L1- and (R,S)-L4-based bimetallic complex catalyst system exhibited the highest catalytic performance to date in terms of enantioselectivity and conversion even in the presence of 0.005 mol % of catalyst (S/C=20 000, turnover number (TON)=17 600). We also studied the tandem silylation or acylation of enantiomerically enriched zinc enolates that formed in situ from copper-L4-complex-catalyzed conjugate addition, which resulted in the high-yield synthesis of chiral silyl enol ethers and enoacetates, respectively. Furthermore, the specialized structure of the present multifunctional N,O,P ligand L1 or L4, and the corresponding mechanistic study of the copper catalyst system were investigated by 31P NMR spectroscopy, circular dichroism (CD), and UV/Vis absorption. Match maker: The chiral bimetallic multinuclear Cu-Zn complex that contains a novel phosphine ligand and bears matching axial and sp3-central chirality from binaphthol and chiral amine was found to be a highly efficient catalyst in the enantioselective conjugate addition of an organic zinc reagent. Copyright

A total synthesis of (-)-antimycin A(3b)

(-)-Antimycin A(3b), the antipode of natural antibiotic antimycin A(3b), was synthesized utilizing the asymmetric aza-Claisen rearrangement. (C) 2000 Elsevier Science Ltd.

Tandem protocol for the stereoselective synthesis of different polyfunctional β-amino acids and 3-amino-substituted carbohydrates

Conjugate addition of homochiral amidocuprates or lithium amides based on (R)-N-(1-phenylethyl)-(trimethylsilyl)amine to α,β-unsaturated esters proceeds stereoselectively and allows the synthesis of β-amino acids. Trapping of the intermediate ester enolate with D2O affords the corresponding deuterated compounds. anti-α-Alkyl-β-amino acids are obtained stereoselectively after transmetalation of the lithium/copper ester enolate to the titanium ester enolate and trapping with carbon electrophiles. Both diastereomers of β-homothreonine, other precursors of 3-amino-substituted carbohydrates, and stereoselectively in position 2 deuterated analogues are formed from enantiomerically pure γ-alkoxy-substituted enoates. The product distribution observed is complementary to published results regarding 1,4- addition to γ-silyloxy-substituted enoates. The anti/syn selectivity can be explained by assuming transition state geometries where the delivery of the nitrogen nucleophile is controlled by lithium 'chelation' between reagent and substrate. In one case the product configuration can be controlled by the reagent irrespective of the substrate stereochemistry, in other cases the topicity of the addition is complementary to published results. For instance, erythro- or threo-configured 2,3-dideoxy-3-aminopentoses are accessible via this route.

Asymmetric Synthesis of β-Amino Acids and α-Deuterated β-Amino Acids via Conjugate Addition of Homochiral Amidocuprates

Conjugate addition of homochiral amidocuprates based on N-trimethylsilylamine or bisamine to α,β-unsaturated esters provides an efficient methodology for the asymmetric synthesis of β-amino acids.Trapping of the inter