644963-35-9

Upstream product

• 1774-47-6 trimethylsulfoxonium iodide 
• 186249-76-3 (R,E)-2-methyl-N-(phenylmethylene)-2-propanesulfinamide 
• 2181-42-2 trimethylsulphonium iodide 
• 937717-76-5 (R_S)-N-[2-chloro-1-phenylethylidene]-tert-butanesulfinamide 
• 937717-90-3 (R_S,S)-N-(2-chloro-1-phenylethyl)-tert-butanesulfinamide 
• 1036645-70-1 (R(S))-N-(2-chloroethylidene)-2-methylpropane-2-sulfinamide 
• 591-51-5 phenyllithium 
• 1591705-09-7 rel-(2S,3R)-1-((S)-tert-butylsulfinyl)-2-chloro-3-phenylaziridine 
• 100-52-7 benzaldehyde 
• 1172578-24-3 C₁₂H₁₆ClNOS 
• 532-27-4 1-chloroacetophenone 

Relevant academic research and scientific papers

Diastereoselective synthesis of 2-methoxyimidoyloxiranes via dimethyl phosphite-mediated coupling of α-keto N-sulfinyl imidates with aldehydes

Dimethyl phosphite-initiated coupling of α-keto N-tert-butylsulfinyl imidates with aldehydes is reported. The epoxide formation involves a cascade transformation initiated by base-promoted addition of phosphite to α-ketoimidates, followed by [1,2]-phospha-Brook rearrangement. This generates α-phosphonyloxy enolates that are subsequently intercepted by aldehydes, leading to [1,4] O→O dialkoxyphosphinyl migration and finally to intramolecular ring closure. This protocol was used to synthesize a range of enantioenriched trans-α,β-epoxy imidates in moderate to high yields with excellent diastereoselectivities.

A preparation of chiral α-chloropivaloyl ethylenimine method

The invention relates to a method for preparing chiral alpha-chloroaziridine. In an organic solvent, the chiral alpha-chloroaziridine is obtained by enabling chiral (Rs)-N-(tertiary butyl sulfonyl) imide, trimethyl (methyl dichloride) silane and alkali to react for 0.5-10h at the temperature of -80 DEG C-30 DEG C. Compared with the prior art, the chiral alpha-chloroaziridine prepared by the method provided by the invention is a potential bioactive molecular synthetic building block and can be used an important intermediate to synthesize a chiral nitrogen-containing compound, such as aziridine. According to the method for preparing the chiral alpha-chloroaziridine, provided by the invention, raw materials used for preparation are economic and easy to obtain, the preparation process conditions are mild, the method is efficient, and the optical purity of the alpha-chloroaziridine prepared by the method is high. The chiral alpha-chloroaziridine prepared by the method provided by the invention is expected to be applied to the fields of asymmetric synthesis and research and development of medicines.

Synthesis of nitrogenated heterocycles by asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)haloimines

Highly optically enriched, protected, nitrogenated heterocycles with different ring sizes have been synthesized by a very efficient methodology consisting of the asymmetric transfer hydrogenation of N-(tert-butylsulfinyl) haloimines followed by treatment with a base to promote an intramolecular nucleophilic substitution process. N-Protected aziridines, pyrrolidines, piperidines, and azepanes bearing aromatic, heteroaromatic, and aliphatic substituents have been obtained in very high yields and diastereomeric ratios up to >99:1. The free heterocycles can be easily obtained by a simple and mild desulfinylation procedure. Both enantiomers of the free heterocycles can be prepared with the same good results by changing the absolute configuration of the sulfur atom of the sulfinyl group.

Terminal aziridines by addition of Grignard reagents or organoceriums to an (α-chloro)sulfinylimine

Reaction of N-(2-chloroethylidene)-tert-butylsulfinamide with Grignard reagents or organoceriums gives terminal N-tert-butylsulfinyl aziridines in good yields and (mainly with organoceriums) good diastereomeric ratios. Oxidation of terminal N-tert-butylsu

Asymmetric synthesis of aziridines by reduction of N-tert-butanesulfinyl α-chloro imines

(Chemical Equation Presented) Reduction of (RS)-N-tert- butanesulfinyl α-halo imines afforded chiral aziridines in good to excellent yields. Upon reduction of (RS)-N-tert-butanesulfinyl α-halo imines with NaBH4 in THF, in

Corey-Chaykovsky Reaction of Chiral Sulfinyl Imines: A Convenient Procedure for the Formation of Chiral Aziridines

The reaction of dimethylsulfonium methylide with a range of aromatic, heterocyclic and aliphatic tert-butylsulfinyl imines is presented. Aziridines were formed in 63-84% yield and 77-95% diastereomeric excess.

Asymmetric aziridination by reaction of chiral N-sulfinylimines with sulfur ylides: Stereoselectivity improvement by use of tert-butylsulfinyl group as chiral auxiliary

Chiral tert-butylsulfinyl group has been shown to be the chiral auxiliary of choice for the asymmetric aziridination of N-sulfinyliminas. Moreover, the sense of the asymmetric induction can be tuned in two ways: the chirality at the tert-butylsulfinyl Sulfur, or the nature of the methylene transfer reagent used. Thus, both aziridines 10(S(S),S) and 10(R(S),R), epimeric at C-2, were obtained in enantiomerically pure form by a single crystallisation (75% yield).