Asymmetric synthesis of 1,2-amino alcohols using (S)-indoline chiral auxiliary.
Chiral hydrazones 1 reacted with aryl- or alkyl-lithiums at -78 degrees C in a short reaction time, within 10 min, to afford arylated or alkylated chiral hydrazines 3 with extremely high diastereoselectivity (up to >99% de) and high chemical yields. The hydrazines are readily converted to chiral amino alcohols 4.
Youn
S W
SW
Department of Chemistry, Korea Advanced Institute of Science and Technology, Taejon, Korea.
Choi
J Y
JY
Kim
Y H
YH
D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry*; D002621:Chemistry / Q000379:methods*; D002851:Chromatography, High Pressure Liquid; D007211:Indoles / Q000737:chemistry; D008094:Lithium / Q000737:chemistry; D008956:Models, Chemical; D013237:Stereoisomerism
D000605:Amino Alcohols; D007211:Indoles; C057812:indoline; D008094:Lithium