2024-03-29T00:09:26Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/195922022-12-12T10:41:24Zcom_10261_31com_10261_3col_10261_284
http://hdl.handle.net/10261/19592
10.1021/jo060465t
19448
Enantiodivergent synthesis of d- and l-erythro-sphingosines through mannich-type reactions of N-benzyl-2,3-O-isopropylidene-d-glyceraldehyde nitrone
American Chemical Society
2006
artículo
Merino, Pedro
rp00481
Jiménez, Pablo
Tejero, Tomás
2006-05
4 pages, 2 schemes, 1 table.-- Supporting Information Available: http://pubs.acs.org.
The addition of a 2-silyloxy silylketene acetal to N-benzyl-2,3-O-isopropylidene-d-glyceraldehyde nitrone (Mannich-type reaction) can be stereocontrolled to give 2S,3S,4S and 2R,3R,4S adducts as major compounds, depending on whether the reaction is activated with zinc(II) triflate or tin(IV) chloride, respectively. The corresponding major adducts were used for preparing diastereomeric polyhydroxy-β-aminoesters that were further converted into suitable orthogonally protected enantiomeric d- and l-erythro-sphingosines.
closedAccess
Journal of Organic Chemistry
2006
71
4685
4688