1356563-72-8

Basic information

• Product Name: (1R,2S)-ethyl 2-chloro-1-methyl-2-((R)-p-tolylsulfinyl)cyclopropanecarboxylate
• Synonyms: (1R,2S)-ethyl 2-chloro-1-methyl-2-((R)-p-tolylsulfinyl)cyclopropanecarboxylate
• CAS NO: 1356563-72-8
• Molecular Weight: 300.806
• Mol File: 1356563-72-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1R,2S)-ethyl 2-chloro-1-methyl-2-((R)-p-tolylsulfinyl)cyclopropanecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S)-ethyl 2-chloro-1-methyl-2-((R)-p-tolylsulfinyl)cyclopropanecarboxylate(1356563-72-8)
• EPA Substance Registry System: (1R,2S)-ethyl 2-chloro-1-methyl-2-((R)-p-tolylsulfinyl)cyclopropanecarboxylate(1356563-72-8)

Safety Data

• Hazardous Substances Data: 1356563-72-8(Hazardous Substances Data)

Upstream product

• 123849-08-1 (-)-(R)-dichloromethyl p-tolyl sulfoxide 
• 97-63-2 methyl methacrylate 

Downstream Products

• 1356563-74-0 1-{(R)-[(1S,2R)-2-(benzyloxymethyl)-1-chloro-2-methylcyclopropyl]sulfinyl}-4-methylbenzene 

Relevant articles and documents

Synthesis of 2-azabicyclo[2.1.0]pentanes by the intramolecular nucleophilic substitution of cyclopropylmagnesium carbenoids with magnesium anilide

A variety of 2-azabicyclo[2.1.0]pentanes were synthesized by the intramolecular nucleophilic substitution of cyclopropylmagnesium carbenoids with magnesium anilide. The 1-chlorocyclopropyl p-tolyl sulfoxides possessing an N-aryl-substituted aminomethyl group were prepared from dichloromethyl p-tolyl sulfoxide, α,β-unsaturated carboxylic acid esters, and anilines in four steps. The deprotonation of the amine with t-BuMgCl followed by sulfoxide/magnesium exchange of the sulfoxides with i-PrMgCl led to the generation of the cyclopropylmagnesium carbenoids possessing a magnesium anilide moiety. Subsequent intramolecular nucleophilic substitution of the cyclopropylmagnesium carbenoids occurred in a 4-exo-tet manner to give the 2-azabicyclo[2.1.0]pentanes. The optically active 2-azabicyclo[2.1.0]pentane was synthesized using a p-tolylsulfinyl group as a chiral auxiliary.

Synthesis, including asymmetric synthesis, of 3-oxabicyclo[3.1.0]hexanes and bicyclo[3.1.0]hexanes by the 1,5-CH insertion of cyclopropylmagnesium carbenoids as the key reaction

The addition reactions of α,β-unsaturated carbonyl compounds with dichloromethyl p-tolyl sulfoxide in the presence of NaHMDS or LDA resulted in the formation of adducts, 1-chlorocyclopropyl p-tolyl sulfoxides bearing a carbonyl group at the 2-position, in almost quantitative yields. The carbonyl group of the adducts was transformed to various ether groups to give 1-chlorocyclopropyl p-tolyl sulfoxides bearing an ether functional group at the 2-position in short steps. Treatment of these products with i-PrMgCl at low temperature afforded cyclopropylmagnesium carbenoids via the sulfoxide-magnesium exchange reaction. 1,5-Carbon-hydrogen insertion (1,5-CH insertion) reaction of the generated magnesium carbenoid intermediates took place to give 3-oxabicyclo[3.1.0]hexanes or bicyclo[3.1.0]hexanes bearing an ether group at the 4-position in moderate to good yields. When this procedure was carried out starting with enantiopure dichloromethyl p-tolyl sulfoxide, enantiopure 3-oxabicyclo[3.1.0]hexanes were obtained in good overall yields. These procedures provide a good way for the synthesis, including asymmetric synthesis, of multisubstituted 3-oxabicyclo[3.1.0]hexanes and bicyclo[3.1.0]hexanes from α,β-unsaturated carbonyl compounds and dichloromethyl p-tolyl sulfoxide in short steps.