252880-50-5

Upstream product

• 54623-66-4 (4S,5S)-(-)-2-chloromethyl-4-methoxymethyl-5-phenyl-2-oxazoline 
• 62731-43-5 9-BBN triflate 
• 52075-14-6 (4S,5S)-(-)-4,5-dihydro-4-methoxymethyl-2-methyl-5-phenyloxazole 

Downstream Products

• 1027205-36-2 1-Chloro-1-((4S,5S)-4-methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-3-methyl-butan-2-ol 
• 252880-35-6 (4S,5S)-2-[(R)-3,3-Bis-(4-methoxy-phenyl)-oxiranyl]-4-methoxymethyl-5-phenyl-4,5-dihydro-oxazole 
• 252880-43-6 (2S,4'S,5'S)-4-methoxymethyl-5-phenyl-2-(3,3-bis-p-tolyloxiranyl)-2-oxazoline 

Relevant academic research and scientific papers

Azaenolates of 2-chloromethyl-4-methoxymethyl-5-phenyl-2-oxazoline - A highly diastereo- and enantioselective synthesis of oxazolinyloxiranes

The oxazoline-derived titanium azaenolate 6 couples highly stereoselectively with aldehydes affording highly optically pure oxazolinyloxiranes 7. The epoxide 7a has been deblocked to form the optically pure formyl oxirane 9. In contrast, the corresponding boron azaenolates 2 and 3 couple with very poor or no stereoselectivity. Lithium, aluminum and tin azaenolates have also been shortly studied.

Highly stereoselective synthesis of optically active oxazolinyl oxiranes from azaenolates of a chiral 2-chloromethyloxazoline

Boron and titanium azaenolates 2 and 4, generated at 0°C and -100°C, respectively, from the optically active chloromethyloxazoline 1, have been found to couple with aliphatic ketones in a highly diastereoselective fashion ending up with the formation of optically active oxazolinyl oxiranes 3. Less stereoselective was the reaction with aromatic ketones. (C) 2000 Elsevier Science Ltd.

Boron azaenolates of chiral oxazolines: Synthesis of optically active formyl oxiranes

Boron azaenolates 2 and 8 from the optically active chloromethyloxazolines 1 and 7 have been found to couple with ketones in a highly diastereoselective fashion, which depends markedly upon the geometry (Z) of the azaenolates and the nature of the ligands which are present on the boron atom, in good accordance with semiempirical calculations (AM1).