T. P. Tang, S. Volkman, J. Ellman
Nov 29, 2001
Citations
3
Influential Citations
80
Citations
Quality indicators
Journal
The Journal of organic chemistry
Abstract
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.