110317-60-7Relevant academic research and scientific papers
Kinetic resolution of isoxazolidines by a Pd-BINAP complex
Ohta, Tetsuo,Kamizono, Hiroyuki,Kawamoto, Aya,Hori, Kazushige,Furukawa, Isao
, p. 3855 - 3863 (2007/10/03)
Asymmetric decomposition of isoxazolidine derivatives under catalysis by optically active palladium(II) complexes was examined. When racemic ethyl cis-2,5-dimethyl-5-phenyl- isoxazolidine-3-carboxylate (cis-la) was treated with a catalytic amount of [Pd(MeCN)2{(S)-TolBINAP}](BF4)2 in CH2Cl2 for 60 h, optically active substrate was recovered with 99% ee and in 48% yield. The highest selectivity was achieved on treatment of racemic ethyl trans-2,4-dimethyl-5,5-di-phenylisoxazolidine-3-carboxylate, to give the optically active substrate in 74% yield with 35% ee. The kf/ks value of this reaction reaches as high as 732. For this decomposition, each substrate should have both a methyl group on the 2-position and an alkoxycarbonyl group on the 3-position of the isoxazolidine ring. The enantioselectivities of the recovered substrates were influenced not only by the other substituent groups on the 4- and 5-positions but also by the geometrical structures of the substrates. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
Ring-Opening of Isoxazolidine Nucleus by Trimethyl Phosphate Treatment: Formation of Tertiary Allylic Alcohols via Intermediate 1,3-Oxazinium Salts
Chiacchio, Ugo,Liguori, Angelo,Romeo, Giovanni,Sindona, Giovanni,Uccella, Nicola
, p. 799 - 817 (2007/10/02)
5,5-Disubstituted isoxazolidines undergo ring opening reaction, leading to tertiary allylic alcohols, by sequential treatment with trimethyl phosphate (TMP) and NaH.The reaction proceeds through sequence steps which involve an initial alkylation to isoxaz
