195379-09-0

Basic information

• Product Name: Oxazole, 2,2'-cyclopropylidenebis[4-(1,1-dimethylethyl)-4,5-dihydro-, (4S,4'S)-
• CAS NO: 195379-09-0
• Molecular Formula: C17H28N2O2
• Mol File: 195379-09-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Oxazole, 2,2'-cyclopropylidenebis[4-(1,1-dimethylethyl)-4,5-dihydro-, (4S,4'S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxazole, 2,2'-cyclopropylidenebis[4-(1,1-dimethylethyl)-4,5-dihydro-, (4S,4'S)-(195379-09-0)
• EPA Substance Registry System: Oxazole, 2,2'-cyclopropylidenebis[4-(1,1-dimethylethyl)-4,5-dihydro-, (4S,4'S)-(195379-09-0)

Safety Data

• Hazardous Substances Data: 195379-09-0(Hazardous Substances Data)

Upstream product

• 10344-69-1 diethyl malonoimidate dihydrochloride 
• 3907-02-6 (2R)-2-amino-3,3-dimethylbutan-1-ol 
• 112245-13-3 (S)-tert-leucinol 
• 34782-60-0 cyclopropane-1,1-dicarboxylic acid dichloride 
• 874916-76-4 (S,S)-N,N'-bis[2-hydroxy-tert-butylethyl]cyclopropane-1,3-dicarboxamide 
• 132098-54-5 (S,S)-2,2'-methylenebis(4-tert-butyl-2-oxazoline) 
• 106-93-4 ethylene dibromide 

Relevant articles and documents

Application of a chiral copper-1,1-bis{2-[(4S)-tert-butyloxazolinyl]} cyclopropane catalyst for asymmetric cyclopropanation of styrene

The structural effects of the bridge moiety and 5-position on bisoxazoline ligands were studied for the copper-catalyzed asymmetric cyclopropanation of styrene with ethyl diazoacetate. The 1,1-bis{2-[(4S)-tert-butyloxazolinyl]} cyclopropane ligand showed a remarkable enhancement in the stereoselectivities (trans/cis = 84/16, >99.9% ee for the trans product) compared with the previously reported best ligand, 2,2-bis{2-[(4S)-tert-butyloxazolinyl]}propane (trans/cis = 75/25, 99.0% ee for the trans product).

Ethynylbenziodazolones (EBZ) as Electrophilic Alkynylation Reagents for the Highly Enantioselective Copper-Catalyzed Oxyalkynylation of Diazo Compounds

Ethynylbenziodoxol(on)e (EBX) cyclic hypervalent iodine reagents are now established reagents for the alkynylation of radicals and nucleophiles, yet they present limited possibilities for further structure and reactivity modification. Herein, the first synthesis is reported for the corresponding ethynylbenziodazolone (EBZ) reagents, in which the oxygen atom in the iodoheterocycle is replaced by a nitrogen atom. The substituent on the nitrogen enables further fine-tuning of the reagent structure and reactivity. EBZ reagents are obtained easily from the corresponding benzamides by using a one-step procedure, and display reactivity comparable to that of EBX reagents. In particular, they are applied in an asymmetric copper-catalyzed oxyalkynylation of diazo compounds, which proceeds in high yield and enantioselectivity for a broad range of substituents on the diazo compounds and the alkyne.

Studies on the bisoxazoline- and (-)-sparteine-mediated enantioselective addition of organolithium reagents to imines

The enantioselective addition of organolithium reagents to N-anisylaldimines promoted by chiral bisoxazolines and (-)-sparteine as external ligands is described. This reaction proceeds readily with a wide range of aldimine substrates (aliphatic, aromatic, olefinic) and organolithium nucleophiles (Me, n-Bu, Ph, vinyl) in excellent yields (81-99%) and with high enantioselectivities (up to 97:3.0 er). The external ligands can be used in substoichiometric amounts albeit with slightly attenuated enantioselectivities. A systematic evaluation of the structural features of the bisoxazolines revealed a primary contribution from the substituent at C(4) and a secondary influence from the bridging substituents. A computational analysis (PM3) provided a clear rationalization for the origin of enantioselectivity.