342651-76-7Relevant academic research and scientific papers
A facile three-step synthesis of 1,2-amino alcohols using the Ellman homochiral tert-butylsulfinamide
Barrow, James C.,Ngo, Phung L.,Pellicore, Janetta M.,Selnick, Harold G.,Nantermet, Philippe G.
, p. 2051 - 2054 (2001)
Addition of organometallic reagents to tert-butylsulfinimines derived from tert-butyldimethylsiloxyacetaldehyde stereoselectively generates protected 1,2-amino alcohols. Removal of the acid labile protecting groups affords amino alcohols in high yield. The predominant diastereomer is opposite to that predicted by the traditional Ellman model; therefore, a chelation model invoking rapid E/Z isomerization of the imine is proposed to rationalize the observed selectivity.
Asymmetric synthesis of protected 1,2-amino alcohols using tert-butanesulfinyl aldimines and ketimines
Tang,Volkman,Ellman
, p. 8772 - 8778 (2007/10/03)
tert-Butanesulfinyl aldimines and ketimines bearing an α-benzyloxy or α-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.
