Details

Autor(en) / Beteiligte

• Mikołajczyk, Marian
• Łuczak, Jerzy
• Sieroń, Lesław
• Wieczorek, Michał W.

Titel

Stereoselective synthesis of both enantiomers of P-chirogenic 2-oxo-2-thio-1,3,2-oxazaphosphorinane tetramethylammonium salt as key precursors to structurally diverse chiral derivatives

Ist Teil von

• Tetrahedron, 2012-01, Vol.68 (1), p.126-132

Ort / Verlag

Kidlington: Elsevier Ltd

Erscheinungsjahr

2012

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• A fully stereoselective synthesis of both enantiomers of 2-oxo-2-thio-1,3,2-oxazaphosphorinanyl salt has been accomplished in five steps with an overall 40–45% yield starting from the diastereoisomeric N-methylstrychninium salts of methyl p-nitrophenyl phosphorothioic acid. Their conversion to the enantiomeric forms of methyl p-nitrophenyl phosphorochloridothionate as a two-step phosphorylating agent allowed the formation of the 1,3,2-oxazaphosphorinane ring in this reaction sequence. An alternative four-step approach to the enantiopure title salt was developed which involves in the first and crucial step cyclocondensation between thiophosphoryl chloride and N-α-naphthylethyl containing a 1,3-aminopropanol group, occurring with almost complete diastereoselectivity. [Display omitted]