An enantioselective and stereodivergent methodology for the synthesis of the four isomers of [3-hydroxy norvaline is presented starting from the common oxazolidin-2-one intermediate 1, via an iterative formation of the oxazolidin-2-one ring to achieve the stereochemical control of the stereogenic centers. The flexibility of the present approach, for the synthesis of several threonine analogs, lies in the ready displacement of thesulfonate group in 2 with the Gfignard reagents in the presence of CuI.
An enantioselective, stereodivergent synthesis of threonine analogs
ZAPPIA, GIOVANNI
1997
Abstract
An enantioselective and stereodivergent methodology for the synthesis of the four isomers of [3-hydroxy norvaline is presented starting from the common oxazolidin-2-one intermediate 1, via an iterative formation of the oxazolidin-2-one ring to achieve the stereochemical control of the stereogenic centers. The flexibility of the present approach, for the synthesis of several threonine analogs, lies in the ready displacement of thesulfonate group in 2 with the Gfignard reagents in the presence of CuI.File in questo prodotto:
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