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Synthesis of Enantiomerically Enriched Amino Sulfide Building Blocks from Acyclic Chiral Amino Allylsilanes (Articolo in rivista)

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Synthesis of Enantiomerically Enriched Amino Sulfide Building Blocks from Acyclic Chiral Amino Allylsilanes (Articolo in rivista) (literal)

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Reginato, Gianna; Pezzati, Bernardo; Ienco, Andrea; Manca, Gabriele; Rossin, Andrea; Mordini, Alessandro (2011)
Synthesis of Enantiomerically Enriched Amino Sulfide Building Blocks from Acyclic Chiral Amino Allylsilanes
in Journal of organic chemistry; American Chemical Society, Washington (Stati Uniti d'America)
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Reginato, Gianna; Pezzati, Bernardo; Ienco, Andrea; Manca, Gabriele; Rossin, Andrea; Mordini, Alessandro (literal)

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Synthesis of Enantiomerically Enriched Amino Sulfide Building Blocks from Acyclic Chiral Amino Allylsilanes (literal)

Abstract

An efficient synthesis of various protected syn-?-sulfenyl amides is described. These are prepared from the corresponding enantiopure amino allylsilanes which are in turn obtained from naturally occurring amino acids. The key step for introduction of the sulfur substituent is a diastereoselective electrophilic sulfodesilylation which is carried out with phthalimidesulfenyl chloride. The resulting homochiral ?-phthalimidesulfenyl amines with an allylic sulforated stereogenic center are useful building blocks, as they represent a starting point for subsequent functional manipulations. (literal)

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