The N-hydroxymethyl group for stereoselective conjugate addition: application to the synthesis of (-)-statine.
[reaction: see text] Efficient synthesis of enantiomerically pure (-)-statine was achieved with the stereoselective intramolecular conjugate addition of the hydroxyl group tethered to the amino group of a configurationally stable N-Boc-L-leucinal derivative.
Yoo
Dongwon
D
School of Chemical Engineering, College of Engineering, Seoul National University, Seoul 151-744, Korea.
Oh
Joon Seok
JS
Kim
Young Gyu
YG
D000596:Amino Acids / Q000138:chemical synthesis*; D003500:Cyclization; D006868:Hydrolysis; D006878:Hydroxides / Q000737:chemistry; D007202:Indicators and Reagents; D017680:Potassium Compounds / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D006878:Hydroxides; D007202:Indicators and Reagents; D017680:Potassium Compounds; C029943:potassium hydroxide; C013165:statine