192764-20-8Relevant academic research and scientific papers
Magnesium chloride (MgCl2) catalyzed highly regioselective C-3 ring opening of 2,3 epoxy alcohols by N-nucleophile
Kumar, Amit,Panda, Gautam
supporting information, (2021/04/09)
We herein report Magnesium chloride (MgCl2) catalyzed first highly C3-selective ring-opening reaction of various 2,3-epoxy alcohols with assorted N-Nucleophiles and sodium azide to furnish 3-amino-1,2 diols and 3-azido-1,2 diols respectively in high yields under mild reaction conditions. This protocol attributes the use of catalytic amount of Magnesium chloride (MgCl2), simple reaction conditions, practical operation and broad functional group tolerance.
Nucleophilic additions of Grignard reagents to N-benzyl-2,3-O- isopropylidene-D-glyceraldehyde nitrone (BIGN). Synthesis of (2S,3R) and (2S,3S)-3-phenylisoserine
Merino, Pedro,Castillo, Elena,Franco, Santiago,Merchan, Francisco L.,Tejero, Tomas
, p. 12301 - 12322 (2007/10/03)
A remarkable Lewis acid tuning has been observed in the nucleophilic addition of Grignard reagent to BIGN, the N-benzyl nitrone derived from 1,2- O-isopropylidene-D-glyceraldehyde. The obtained α,β-dialkoxy hydroxylamines can serve as starting points for the synthesis of both aminodiols and α- hydroxy-β-amino acids. This synthetic approach is illustrated by the synthesis of the antipode of the C-13 side chain of Taxotere as well as its C-3 epimer.
Stereocontrolled addition of Grignard reagents to α-alkoxy nitrones. Synthesis of syn and anti 3-amino-1,2-diols
Merino, Pedro,Castillo, Elena,Merchan, Francisco L.,Tejero, Tomas
, p. 1725 - 1729 (2007/10/03)
The stereoselective addition of Grignard reagents to α-alkoxy nitrones has been achieved with excellent stereocontrol using ZnBr2 and Et2AlCl as precomplexing agents to obtain the corresponding syn- and anti- adducts, respectively. The obtained hydroxylamines have been transformed into valuable 3-amino-1,2-diols.
