207676-58-2

Upstream product

• 100-52-7 benzaldehyde 
• 92288-03-4 (4R)-4-phenyl-3-vinyl-oxazolidin-2-one 
• 90319-52-1 (4R)-phenyl-2-oxazolidinone 

Downstream Products

• 3182-95-4 L-Phenylalaninol 
• 207676-65-1 (-)-3-[2-(1-hydroxy-3-phenylpropyl)]-4-phenyloxazolidin-2-one 

Relevant academic research and scientific papers

Facial diastereoselectivity in the photocycloaddition of chiral N-acyl enamines to benzaldehyde

The facial diastereoselectivity in the photocycloaddition of the chiral N-acyl enamines 5, 6, and 7 to benzaldehyde has been studied. The anamide 5 derived from α-phenylethylamine (8) gave the corresponding oxetanes in good total yield (74%) but the diastereofacial selection was unsatisfactory (32% de). The N-vinyloxazolidinones 6 and 7 were prepared from the parent chiral 4-phenyl- (11) or 4-benzyloxazolidinone (15) by vinylation. Their photocycloadditons to benzaldehyde proceeded smoothly and yielded the corresponding oxetanes 12 and 16 (70-80%). A remarkable discrepancy in the course of the reaction was observed. Whereas oxetane formation from 6 proceeded with low diastereoselectivity (30% de) the Paterno-Buchi reaction of compound 7 gave predominantly one diastereoisomer 16a (62% de) the relative configuration of which was opposite to the major diastereomer 12a obtained from oxazolidinone 6.