92241-13-9Relevant academic research and scientific papers
Diastereofacial Selectivity Studies on 3-Alkenyl-4,5-diphenyl-4,5-dihydroisoxazoles
Wade, Peter A.,Bereznak, James F.,Palfey, Bruce A.,Carroll, Patrick J.,Dailey, William P.,Sivasubramanian, S.
, p. 3045 - 3051 (2007/10/02)
Epoxidation of 3-(1-phenylethenyl)-4,5-diphenyl-4,5-dihydroisoxazole and 3-ethenyl-4,5-diphenyl-4,5-dihydroisoxazole occurred with 74percent diastereomer excess (de) and 66percent de, respectively.Catalytic cis-hydroxylation of the 3-(1-phenylethenyl)dihydroisoxazole afforded a diol with 80percent de.Cycloaddition reactions of the same alkenyl dihydroisoxazoles with bromonitrile oxide and phenylsulfonylcarbonitrile oxide occurred with 10-46percent de; opposite diastereomers were preferred in the reactions of 3-ethenyl- and 3-(1-phenylethenyl)dihydroisoxazoles.These results are rationalized based on a combination of two factors: a preference for the s-trans heterodiene conformer and a preference for attack anti to the C-4 phenyl group in all but one case.The s-trans conformer of 3-ethenyl-4,5-dihydroisoxazole was determined by the ab initio method to be 2.8 kcal/mol more stable than the s-cis conformer.
Acid-Catalyzed Nitronate Cycloaddition Reactions. Useful Syntheses and Simple Transformations of 3-Acyl- and 3-Alkenylisoxazolines
Wade, Peter A.,Amin, Nayan V.,Yen, Hwa-Kwo,Price, David T.,Huhn, George F.
, p. 4595 - 4601 (2007/10/02)
Nitronic esters derived from primary nitro ketones, ethyl nitroacetate, and (phenylsulfonyl)nitromethane react with dipolarophiles in the presence of nonaqueous protic and Lewis acids to give nitrile oxide cycloadducts. α-Nitro ketones, ethyl nitroacetate
