Tetrahedron Letters p. 2853 - 2856 (1999)
Update date:2022-08-24
Topics:
Goti, Andrea
Cacciarini, Martina
Cardona, Francesca
Brandi, Alberto
Optimization of a strategy providing the enantiomerically pure nitrone 2 in five steps and 28% overall yield from L-malic acid has been achieved by the combined use of DIBAL-H as the reductant and triisopropylsilyl as the protecting group. The utility of nitrone 2 as synthetic intermediate is demonstrated by a ready access to polyhydroxylated indolizidines and pyrrolizidines via stereoselective 1,3-dipolar cycloaddition reactions.
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