One-step highly diastereoselective synthesis of gamma-aminoalkyl-substituted gamma-butyrolactones by an asymmetric samarium-mediated ketyl-alkene coupling reaction.
The samarium(II) iodide mediated reaction of N,N-dibenzyl-protected (S)-alpha-amino aldehydes with (1S,2R)-N-methylephedrinyl acrylate gave the (4R,1'S)-gamma-(aminoalkyl)-gamma-butyrolactones in good yields with high diastereoselectivities (up to 80% de); (4R,1'S)-gamma-amino-(2-phenylethyl)-gamma-butyrolactone (6a), which should be a potent precursor for gamma-secretase inhibitors, was obtained with high de value.
Fukuzawa
Shin-ichi
S
Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.
Miura
Manabu
M
Saitoh
Takahide
T
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000032:analysis / Q000138:chemical synthesis*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012493:Samarium / Q000737:chemistry; D013237:Stereoisomerism
D007202:Indicators and Reagents; D012493:Samarium; D015107:4-Butyrolactone