288089-62-3

Upstream product

• 112245-13-3 (S)-tert-leucinol 
• 100-47-0 benzonitrile 
• 928150-62-3 N-(α,α-difluorobenzyl)pyrrolidine 
• 3389-54-6 n-benzoylpyrrolidine 
• 504-77-8 4,5-dihydro-1,3-oxazol 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 624-95-3 3,3-dimethylbutanol 
• 26630-25-1 N-phenoxybenzimidic acid chloride 

Downstream Products

• 642491-11-0 C₃₂H₃₇N₂O₂P 
• 1039038-25-9 (S)-4-tert-butyl-2-(2-iodophenyl)-4,5-dihydrooxazole 

Relevant academic research and scientific papers

Homochiral cyclopalladated complexes of (S)-4-tert-butyl-2-phenyl-2-oxazoline. X-ray study of (S,S)-di-μ-chlorobis-{2-[2-(4-tert-butyl)oxazolinyl]phenyl-C,N} dipalladium(II)

Due to steric promotion of C-H bond activation, the direct ortho-palladation of (S)-4-tert-butyl-2-phenyl-2-oxazoline using Pd(OAc)2 in AcOH provided (S,S)-di- μ-acetatobis-[2-(2-(4-tert-butyl) oxazolinyl)phenyl-C,N]dipalladium(II) (2) in an ex

Phosphorus-Based Organocatalysis for the Dehydrative Cyclization of N-(2-Hydroxyethyl)amides into 2-Oxazolines

A metal-free, biomimetic catalytic protocol for the cyclization of N-(2-hydroxyethyl)amides to the corresponding 2-oxazolines (4,5-dihydrooxazoles), promoted by the 1,3,5,2,4,6-triazatriphosphorine (TAP)-derived organocatalyst tris(o-phenylenedioxy)cyclotriphosphazene (TAP-1) has been developed. This approach requires less precatalyst compared to the reported relevant systems, with respect to the phosphorus atom (the maximum turnover number (TON) ～30), and exhibits a broader substrate scope and higher functional-group tolerance, providing the functionalized 2-oxazolines with retention of the configuration at the C(4) stereogenic center of the 2-oxazolines. Widely accessible β-amino alcohols can be used in this approach, and the cyclization of N-(2-hydroxyethyl)amides provides the desired 2-oxazolines in up to 99% yield. The mechanism of the reaction was studied by monitoring the reaction using spectral and analytical methods, whereby an 18O-labeling experiment furnished valuable insights. The initial step involves a stoichiometric reaction between the substrate and TAP-1, which leads to the in situ generation of the catalyst, a catechol cyclic phosphate, as well as to a pyrocatechol phosphate and two possible active intermediates. The dehydrative cyclization was also successfully conducted on the gram scale.

Enantioselective radical C–H amination for the synthesis of β-amino alcohols

Asymmetric, radical C–H functionalizations are rare but powerful tools for solving modern synthetic challenges. Specifically, the enantio- and regioselective C–H amination of alcohols to access medicinally valuable chiral β-amino alcohols remains elusive. To solve this challenge, a radical relay chaperone strategy was designed, wherein an alcohol was transiently converted to an imidate radical that underwent intramolecular H-atom transfer (HAT). This regioselective HAT was also rendered enantioselective by harnessing energy transfer catalysis to mediate selective radical generation and interception by a chiral copper catalyst. The successful development of this multi-catalytic, asymmetric, radical C–H amination enabled broad access to chiral β-amino alcohols from a variety of alcohols containing alkyl, allyl, benzyl and propargyl C–H bonds. Mechanistic experiments revealed that triplet energy sensitization of a Cu-bound radical precursor facilitates catalyst-mediated HAT stereoselectivity, enabling the synthesis of several important classes of chiral β-amines by enantioselective, radical C–H amination. [Figure not available: see fulltext.]

Intramolecularly sulfur-stabilized silicon cations as Lewis acid catalysts

The synthesis and spectroscopic characterization of previously unprecedented sulfur-stabilized silicon cations are reported. Several 1,3-dithiolan-2-yl- and 1,3-dithian-2-yl-substituted silanes were prepared and successfully transformed into the corresponding silicon cations by hydride abstraction. The silicon-sulfur interaction creates three consecutive stereocenters at three different elements. It is remarkable that the present stereocenter at the silicon atom determines the stereochemical outcome at the formerly prochiral sulfur and carbon atoms with excellent diastereoselectivity. All sulfur-stabilized silicon cations are shown to be potent catalysts in a challenging Diels-Alder reaction. Moreover, structurally related oxazoline-stabilized silicon cations were generated and characterized but found to be unreactive.

Synthesis of N,P-, S,P-, P,P- and S,P,S-ligands using reactions of cyclopalladated complexes with KPPh2

Readily available air- and moisture-stable dimeric chloro-bridged CN-, CS- and CP-cyclopalladated complexes with the (sp2)C-Pd bond react with 4.5 equiv. of KPPh2 in THF to give the corresponding P,N-, P,S- and P,P-bidentate ligands

SYNTHESIS OF OXAZOLINE COMPOUNDS

The present invention provides an improved process for preparing an oxazoline compound of the formula: (I) wherein R1 and R2 are independently hydrogen, sulfide, sulfoxide, sulfonyl, optionally substituted lower alkyl, optionally sub

A facile synthesis of oxazolines, thiazolines, and imidazolines using α,α-difluoroalkylamines

β-Amino alcohols, β-amino thiols, and β-diamines can be converted to the corresponding oxazoline, thiazoline, and imidazoline derivatives, respectively, by reaction with α,α-difluoroalkylamines under mild conditions. The reaction is applicable for the synthesis of optically active heterocyclic compounds. Georg Thieme Verlag Stuttgart.

Diastereoselective transformation of arenes into highly enantiomerically enriched substituted cyclohexadienes

Sequential addition of a C-nucleophile and a C-electrophile to enantiomerically pure arene tricarbonyl chromium complexes 3a,b, 6, and 8b, containing aryl bound chiral oxazoline, SAMP-hydrazone and chiral imine auxiliaries affording substituted cyclohexadienes. C-Nucleophiles included alkyl-, vinyl-, and phenyl-lithium reagents. C-Electrophiles included methyl iodide, allyl bromide, benzyl bromide, and propargyl bromides. The 1,3-cylohexadienes were obtained with a 1,5,6-substitution pattern. The results are consistent with a diastereoselective exo-nucleophilic addition to an ortho position of the complexed arene, followed by addition of the electrophile to the metal center. With allyl, ben-zyl, and propargyl groups, direct reductive elimination then yielded trans-5,6-substituted products. With methyl iodide, reductive elimination was preceded by CO insertion and acetyl cyclohexadienes were formed exclusively whose in situ deprotonation/alkylation gave products in which three C-substituents had been added across an arene double bond with complete regio- and stereocontrol. The two path-ways reflect migratory aptitude to carbonylation. An X-ray structure determination of the phenyl oxazoline complex 3a allowed a rationalization of observed diastereoselectivity. Asymmetric induction was very high with the oxazoline and the SAMP-hydrazone complexes (>90% de) whereas the chiral benzaldehyde imine complex 8b afforded the substituted diene aldehydes in moderate enantiomeric purity (34-58% ee). Changing the reaction medium from THF to toluene in reactions with 8b resulted in products of the opposite chirality.