Asymmetric synthesis of protected 1,2-amino alcohols using tert-butanesulfinyl aldimines and ketimines.
tert-Butanesulfinyl aldimines and ketimines bearing an alpha-benzyloxy or alpha-silyloxy substituent serve as precursors in the synthesis of protected 1,2-amino alcohols in high yields and diastereoselectivities. General protocols are described for the addition of unbranched alkyl, branched alkyl, and aryl organometallic reagents to N-sulfinyl aldimines 1 and 2 and ketimines 5 and 6. Furthermore, the selective N- or O-deprotection of sulfinamide products 3, 4, 7, and 8 is described, enabling further synthetic transformations of the reaction products.
Tang
T P
TP
Department of Chemistry, University of California-Berkeley, Berkeley, CA 94720-1460, USA.
Volkman
S K
SK
Ellman
J A
JA
D000605:Amino Alcohols / Q000138:chemical synthesis*; D007097:Imines / Q000737:chemistry*; D007202:Indicators and Reagents; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism; D013441:Sulfinic Acids / Q000737:chemistry*
D000605:Amino Alcohols; D007097:Imines; D007202:Indicators and Reagents; D009942:Organometallic Compounds; D013441:Sulfinic Acids