Diastereoselective catalytic asymmetric nitroaldol reaction utilizing rare earth-Li-(R)-BINOL complex. A highly efficient synthesis of norstatine
1994; Elsevier BV; Volume: 35; Issue: 33 Linguagem: Inglês
10.1016/0040-4039(94)88093-x
ISSN1873-3581
AutoresHiroaki Sasai, Won-Sup Kim, Takeyuki Suzuki, Masakatsu Shibasaki, Masaru Mitsuda, Junzo Hasegawa, Takehisa Ohashi,
Tópico(s)Synthesis and Catalytic Reactions
ResumoRare earth-Li-BINOL complexes were used to catalyze nitroaldol reactions of optically active α-amino-aldehydes with nitromethane in a highly diastereoselective manner. A typical adduct, (2S, 3S)-3-phthaloylamino-2-hydroxy-1-nitro-4-phenylbutane was conveniently converted to (2S, 3S)-3-amino-2-hydroxy-4-phenylbutanoic acid (erythro-AHPA ; phenylnorstatine), a component of the HIV protease inhibitor KNI-227 and KNI-272.
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