174302-74-0Relevant articles and documents
re- and si-face-selective nitroaldol reactions catalyzed by a rigid chiral quaternary ammonium salt: A highly stereoselective synthesis of the HIV protease inhibitor amprenavir (Vertex 478)
Corey,Zhang, Fu-Yao
, p. 1931 - 1934 (1999)
Either amprenavir (1) or its C(2) diastereomer can be synthesized in a simple way by the use of a nitroaldol reaction carried out in the presence of one or the other of the two ammonium ions 2. The 1,3-diamino-2-hydroxypropyl structural element of 1 is also found in many other peptidomimetics and HIV protease inhibitors. Described here is a new strategy for possible application to direct and stereocontrolled synthesis of such compounds.
Formation of multi-stereogenic centers using a catalytic diastereoselective Henry reaction
Arai, Takayoshi,Taneda, Yoshinori,Endo, Yoko
supporting information; experimental part, p. 7936 - 7938 (2011/01/04)
A diastereoselective Henry reaction of chiral aldehydes with nitroalkanes was developed using a chiral sulfonyldiamine (L1)-CuCl complex. The reaction of (R)-2-phenylpropanal and nitromethane was smoothly catalyzed by the (S,S,S)-L1-CuCl complex to give the adduct with 99/1 syn/anti selectivity in 99% ee. In the reaction of (S)-2-phenylpropanal and nitroethane, the (R,R,R)-L1-CuCl catalyst yielded the expected three contiguous stereogenic centers in a highly syn-selective Henry reaction.
Diastereoselective catalytic asymmetric nitroaldol reaction utilizing rare earth-Li-(R)-BINOL complex. A highly efficient synthesis of norstatine
Sasai,Sasai, Hiroaki,Kim,Kim, Won-Sup,Suzuki,Suzuki, Takeyuki,Shibasaki,Shibasaki, Masakatsu,Mitsuda,Mitsuda, Masaru,Hasegawa,Hasegawa, Junzo,Ohashi,Ohashi, Takehisa
, p. 6123 - 6126 (2007/10/02)
Rare 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-phtaloylamino-2-hydroxy-1-nitro-4-phenylbutane was conveni
