Tetrahedron Letters p. 3727 - 3730 (1999)
Update date:2022-07-30
Topics:
Roussi, Fanny
Bonin, Martine
Chiaroni, Angele
Micouin, Laurent
Riche, Claude
Husson, Henri-Philippe
Chiral non racemic carbazate 1, derived from (R)-(-)-phenylglycinol, reacts regioselectively with benzaldehyde or its dimethylacetal to give an azomethine imine. The facial, endo/exo and regio selectivities of 1,3- dipolar cycloadditions of this reactive species with various dipolarophiles have been studied and are described in this paper. In the best cases, up to three contiguous asymmetric centers could be generated simultaneously, in a complete enantio- and diastereoselective fashion.
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