75866-72-7

Usage

Uses

Used in Asymmetric Synthesis:
(S)-4-Benzyl-2-methyl-2-oxazoline is utilized as a chiral auxiliary, a crucial component in enhancing the selectivity of reactions involving the formation of chiral molecules. Its application in this field is significant for producing enantiomerically pure compounds, which are essential in various industries, including pharmaceuticals.
Used in Organometallic Chemistry:
In organometallic chemistry, (S)-4-Benzyl-2-methyl-2-oxazoline acts as a ligand, bonding with metal atoms to form complexes that can catalyze a range of chemical reactions. Its use in this area is vital for the development of new catalysts and the advancement of synthetic methods.
Used in Pharmaceutical Synthesis:
(S)-4-BENZYL-2-METHYL-2-OXAZOLINE serves as a building block in the synthesis of various pharmaceuticals and other fine chemicals. Its incorporation into the structure of these compounds can influence their biological activity, making it a valuable asset in drug discovery and development.
Used in Chiral Resolving:
(S)-4-Benzyl-2-methyl-2-oxazoline is employed as a chiral resolving agent, facilitating the separation of enantiomers, which is critical in the production of single-enantiomer drugs. The distinct properties of each enantiomer can lead to different effects in biological systems, making the ability to separate them a crucial aspect of pharmaceutical development.
Used in Asymmetric Catalysis:
As a participant in asymmetric catalysis, (S)-4-Benzyl-2-methyl-2-oxazoline contributes to the development of more efficient and selective catalysts. This application is essential for enhancing the yield and selectivity of chemical reactions, particularly in the synthesis of complex molecules like pharmaceuticals and agrochemicals.

InChI:InChI=1/C11H13NO/c1-9-12-11(8-13-9)7-10-5-3-2-4-6-10/h2-6,11H,7-8H2,1H3/t11-/m0/s1

Upstream product

• 3182-95-4 L-Phenylalaninol 
• 2208-07-3 ethyl acetimidate hydrochloride 
• 132836-66-9 (S)-3-acetyl-4-benzyloxazolidin-2-one 
• 73058-30-7 (2S)-2-benzylazacyclopropane 
• 78-39-7 Triethyl orthoacetate 
• 52485-51-5 N-[(1S)-1-benzyl-2-hydroxyethyl]acetamide 
• 75866-60-3 (+)-1-(acetyl)-2(S)-benzylaziridine 

Downstream Products

• 116173-83-2 [(R)-1-((S)-4-Benzyl-4,5-dihydro-oxazol-2-ylmethyl)-2-methyl-propyl]-carbamic acid methyl ester 
• 116173-83-2 [(S)-1-((S)-4-Benzyl-4,5-dihydro-oxazol-2-ylmethyl)-2-methyl-propyl]-carbamic acid methyl ester 
• 190260-35-6 (4S)-4-benzyl-2-methyl-2-thiazoline 
• 474669-68-6 (Rs,S)-4-benzyl-2-(p-toluenesulfinylmethyl)-1,3-oxazoline 

Relevant academic research and scientific papers

Palladium-Catalyzed Amide-Directed Enantioselective Hydrocarbofunctionalization of Unactivated Alkenes Using a Chiral Monodentate Oxazoline Ligand

A Pd-catalyzed amide-directed enantioselective hydrocarbofunctionalization of unactivated alkenes with C-H nucleophiles has been developed using a chiral monodentate oxazoline (MOXin) ligand. Various indoles react at C3 position with aminoquinoline-coupled 3-alkenamides to give γ addition products in good to excellent yield and enantioselectivity. This study represents an important advance of the development of chiral monodentate oxazoline ligands, which have been underexplored for asymmetric catalysis.

Decarboxylative isomerization of N-Acyl-2-oxazolidinones to 2-oxazolines

(Chemical Equation Presented) N-Acyl-2-oxazolidinones are ring-opened by lithium iodide and decarboxylated in the presence of a mild proton source. Further reaction with an amine base provides 2-oxazolines. The transformation is general for oxazolidinones unsubstituted in the 5 position and occurs under mild conditions (25-50°C). These results complement the existing methods for this transformation by allowing lower temperatures and/or avoiding metal catalysts.

Synthesis and structural characterization of enantiopure exo and endo six-membered oxazoline-derived palladacycles

Direct palladation of (S)-4-benzyl-2-methyl-2-oxazoline (1) and (S)-2-benzyl-4-tert-butyl-2-oxazoline (2) using Pd(OAc)2 in MeCN afforded the corresponding μ-acetato-dimeric complexes with six-membered exo and endo palladacycles, respectively. The same complexes were obtained by reacting coordination complexes Pd(1)2(OAc)2 and Pd(2)2(OAc)2 with Pd(OAc)2 in MeCN. Metalation of (S)-2,4-dibenzyl-2-oxazoline (3) with Pd(OAc)2 in AcOH, MeCN or CH2Cl2 resulted in the regiospecific formation of the six-membered endo palladacycle. The obtained μ-acetato-dimeric complexes were converted to the corresponding μ-chloro-dimeric derivatives 7, 11 and 13 by treatment with LiCl in acetone. The mononuclear PPh3 adducts 8, 12 and 14 were obtained by reacting dimers 7, 11 and 13 with PPh3 in benzene. NMR spectroscopy data supported the proposed structures of all complexes and suggested that exo and endo palladacycles in 8 and 12 have rigid boat conformations in CHCl3. The X-ray crystal structures of the μ-acetato dimer 6 with the exo palladacycle and the PPh3 adduct 14 with the endo metalacycle revealed boat conformation of both palladacycles and chiral twisted conformations δ(S) and λ(S), respectively, of the oxazoline rings in the solid state.

Lewis acid-catalyzed asymmetric diels-alder reactions using chiral sulfoxide ligands: chiral 2-(arylsulfinylmethyl)-1,3-oxazoline derivatives.

New chiral sulfoxide-1,3-oxazoline ligands have been developed as chiral ligands for Lewis acid-catalyzed asymmetric Diels-Alder reactions. The use of chiral sulfinyl 1,3-oxazoline ligands in copper(II)-catalyzed asymmetric Diels-Alder reactions provided an endo cycloadduct as a major product with moderate enantioselectivity. A rationale is proposed for the mechanism of the asymmetric induction.

Synthesis and oxidation of chiral 2-thiazolines (4,5-dihydro-1,3-thiazoles)

Eight new chiral 2-thiazolines (4,5-dihydro-1,3-thiazoles) 2 have been prepared by treatment of the 2-methyloxazolines 1, the benzoylamino alcohols 4 or the trimethylacetylamino alcohols 5 with P2S5. With a 2-methyl substituent, reaction with Oxone results in ring-opening to give the acetylamino disulfides 9 and with MCPBA there is also ring-opening with incorporation of a m-chlorobenzoyl group to give 12. Treatment of the 2-phenyl compounds with a variety of oxidants gives the benzoylamino sulfonic acids 10 and the disulfides 9 together with the thiazoles 11 in varying proportions. The sulfonic acids and thiazoles are obtained in pure form by reaction with 3 equiv. of peracetic acid and with sulfur, respectively. Although reaction of 2d-f with KMnO4 under phase-transfer conditions gives the thiazoles 11, addition of 1 equiv. of benzoic acid results in a complete change in selectivity to afford the thiazoline 1,1-dioxides 3d-f in excellent yield. These compounds prove to be exceptionally moisture-sensitive and readily hydrolyse to give the benzoylamino sulfinic acids 8 whose further oxidation and disproportionation probably explains the formation of the sulfonic acids and disulfides with the other oxidants. The high reactivity of the sulfones 3 towards nucleophilic ring-opening precludes their deprotonation and alkylation. Upon flash vacuum pyrolysis at 600°C, they fragment to give SO2, benzonitrile and the alkenes 16 in high yield. Fully assigned 13C NMR spectra are presented for the 18 heterocyclic compounds prepared and for 17 acyclic derivatives.

(DIETHYLAMINO)SULFUR TRIFLUORIDE (DAST) AS A USEFUL REAGENT FOR THE PREPARATION OF 2-OXAZOLINES FROM 1,2-AMIDO ALCOHOLS

Acylic 1,2-amido alcohols (6) react efficiently with a slight excess of (diethylamino)sulfur trifluoride (DAST) to afford the corresponding 2-oxazolines (10) in good yields ranging between 57-95percent.Even at the low temperature of -78 deg C, a rapid ( 1 h) and stereoselective amide cyclization is observed without formation of acylaziridine by-products.The scope of this cyclization is discussed.

A mild, general preparation of N-acyl aziridines and 2-substituted 4(S)-benzyloxazolines

The conversion of a wide range of carboxylic acids into their acyl imidazolides with subsequent addition of an aziridine rapidly gives a quantitative yield of the corresponding N-acyl aziridines.Iodide (or bromide) ion catalysed rearrangement of N-acyl 2(S)-benzylaziridines 1 to oxazolines 6 proceeds quantitatively.