Condensation of the lithium salt of (R)-methyl p-tolyl sulfoxide 1 with fluorinated N,P-unsaturated ketones 2 leads to (3 R/S,R,)-(E)- 1- ethoxy-3-fluoroalkyl-3-hydroxy-4-(4-methylphenylsulfinyl)b1u- te-n es 3, whose absolute stereochemistry was determined by X-ray diffraction and NMR analyses. Reductive removal of the sulfinyl chiral auxiliary allows the preparation of both enantiomers of fluorinated tertiary alcohols of type 8 and 9.
SYNTHESIS AND USE OF (E)-1-ETHOXY-3-FLUOROALKYL-3-HYDROXY-4-(-4-METHYLPHENYLSULFINYL)BUT-1-ENES
BRAVO, PIERFRANCESCO;BRUCHE', LUCA ALFREDO CASIMIRO;MEILLE, STEFANO VALDO;
1995-01-01
Abstract
Condensation of the lithium salt of (R)-methyl p-tolyl sulfoxide 1 with fluorinated N,P-unsaturated ketones 2 leads to (3 R/S,R,)-(E)- 1- ethoxy-3-fluoroalkyl-3-hydroxy-4-(4-methylphenylsulfinyl)b1u- te-n es 3, whose absolute stereochemistry was determined by X-ray diffraction and NMR analyses. Reductive removal of the sulfinyl chiral auxiliary allows the preparation of both enantiomers of fluorinated tertiary alcohols of type 8 and 9.File in questo prodotto:
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Pub064Bravo sulfinyl bute Perkin 1995.pdf
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